Metal complex and use thereof

ABSTRACT

The present invention relates to a metal complex and application thereof. The metal complex has a general formula of Ir(La)(Lb)(Lc), and includes a structure as shown in the following formula (1) as a ligand La. The metal complex provided in the present invention has the advantages of high optical and electrical stability, high luminescence efficiency, long service life, and high color saturation, and can be used in organic light-emitting devices. In particular, the metal complex has the potential for application in the AMOLED industry as a red light-emitting phosphorescent material.

TECHNICAL FIELD

The present invention relates to the technical field of organic electroluminescence, in particular to an organic light-emitting material applicable to organic electroluminescent devices, and specially in particular to a metal complex and application thereof in an organic electroluminescent device.

BACKGROUND

At present, as a new-generation display technology, an organic electroluminescent device (OLED) has attracted more and more attention in display and lighting technologies, thus having a wide application prospect. However, compared with market application requirements, properties, such as luminescence efficiency, driving voltage, and service life of OLED devices still need to be strengthened and improved.

In generally, the OLED devices include various organic functional material films with different functions between metal electrodes as basic structures, which are similar to sandwich structures. Under the driving of a current, holes and electrons are injected from a cathode and an anode, respectively. After moving a certain distance, the holes and the electrons are compounded in a light-emitting layer, and then released in the form of light or heat to achieve luminescence of the OLED.

However, organic functional materials are core components of the OLED devices, and the thermal stability, photochemical stability, electrochemical stability, quantum yield, film forming stability, crystallinity, and color saturation of the materials are main factors affecting properties of the devices. In general, the organic functional materials include fluorescent materials and phosphorescent materials. The fluorescent materials are usually organic small-molecule materials, which can only use 25% of singlet luminescence, thus having low luminescence efficiency. Meanwhile, due to a spin-orbit coupling effect caused by a heavy atom effect, the phosphorescent materials can use 25% of a singlet state, and can also use 75% of energy of a triplet exciton, so that the luminescence efficiency can be improved. However, compared with the fluorescent materials, the phosphorescent materials are started later, and the thermal stability, service life, and color saturation of the materials need to be improved. Thus, the phosphorescent materials are a challenging topic. Various organometallic compounds have been developed to serve as the phosphorescent materials. For example, according to an invention patent document CN107973823, a quinoline iridium compound is disclosed. However, the color saturation and device properties, especially luminescence efficiency and device service life, of the compound need to be improved. According to an invention patent document CN106459114, an iridium compound coordinated with a β-dione coordination group is disclosed. However, the compound has high sublimation temperature and low color saturation. In particular, the device performance is unsatisfactory, which needs to be further improved. According to an invention patent CN109721628, a compound with a fluorenyl thiophenpyrimidine structure and an organic electroluminescent device and compound including the above compound are disclosed.

However, a novel material capable of further improving properties of organic electroluminescent devices is still expected to be developed.

SUMMARY

Objectives of the present invention are to provide an organic electroluminescent device with high properties and to provide a novel material capable of realizing the organic electroluminescent device.

In order to achieve the above objectives, the inventor has conducted in-depth studies repeatedly and found that an organic electroluminescent device with high properties can be obtained by using a metal complex including a structure as shown in the following formula (1) as a ligand.

One of the objectives of the present invention is to provide a metal complex. The metal complex has the advantages of high optical and electrochemical stability, high color saturation, high luminescence efficiency, and long service life, and can be used in organic electroluminescent devices. In particular, the metal complex has the potential for application in the OLED industry as a red light-emitting dopant.

A metal complex has a general formula of Ir(La)(Lb)(Lc), and includes a ligand La as shown in the following formula (1),

-   -   where among A₁-A₄, one group is a C—C bond connected to an E         ring, one group is a C-metal bond connected to a metal, one         group is CR₄, and the other group is CR₀ or N; among A₅-A₈, one         group is CR₃, and the other three groups independently refer to         CR₀ or N;     -   the number of R1-R2 is a maximum substitution number;     -   R₀-R₄ are independently selected from hydrogen, deuterium,         halogen, substituted or unsubstituted C₁-C₁₀ alkyl, substituted         or unsubstituted C₃-C₂₀ cycloalkyl, substituted or unsubstituted         C₁-C₁₀ heteroalkyl, substituted or unsubstituted C7-C₃₀ aralkyl,         substituted or unsubstituted C₁-C₁₀ alkoxy, substituted or         unsubstituted C₆-C₃₀ aryloxy, substituted or unsubstituted         C₂-C₂₀ alkenyl, substituted or unsubstituted C₃-C₃₀ silyl,         substituted or unsubstituted C₆-C₃₀ aryl, substituted or         unsubstituted C₃-C₃₀ heteroaryl, substituted or unsubstituted         C₃-C₃₀ arylsilyl, substituted or unsubstituted C₀-C₂₀ amino,         cyano, nitrile, isonitrile, and phosphino; at least one of R₃         and R₄ is not hydrogen; when A₇ is CR₀, R₀ is not F;     -   X is independently selected from O, S, Se, C(R)₂, Si(R)₂, NR,         BR, and POR; the R is independently selected from substituted or         unsubstituted C₁-C₁₀ alkyl or alkoxy, substituted or         unsubstituted C₂-C₃₀ cycloalkyl, substituted or unsubstituted         C₆-C₃₀ aryl, and substituted or unsubstituted C₁-C₁₈ heteroaryl;     -   the “substituted” refers to substitution with deuterium, F, Cl,         Br, C1-C₄ alkyl, C1-C₄ alkoxy, C3-C₆ cycloalkyl, amino         substituted with C1-C₄ alkyl, cyano, nitrile, isonitrile, and         phosphino;     -   a heteroatom in the heteroalkyl or heteroaryl is at least one of         S, O, and N;     -   a dotted line refers to a bond connected to metal iridium;     -   La, Lb, and Lc are different from each other, and any two of the         three groups are connected to form a multidentate ligand, or the         three groups are connected by a group; both the Lb and the Lc         are a monoanionic bidentate ligand;     -   and the “different from each other” refers to having different         parent nucleus structures, having a same parent nucleus         structure with different substituents, or having a same parent         nucleus structure with a same substituent at different         positions.

Preferably, the metal complex has a structure as shown in the following formula (2):

-   -   where the A is CR₀ or N; the R₀-R₄ are independently selected         from hydrogen, deuterium, halogen, substituted or unsubstituted         C₁-C₁₀ alkyl, substituted or unsubstituted C₃-C₂₀ cycloalkyl,         substituted or unsubstituted C₁-C₁₀ heteroalkyl, substituted or         unsubstituted C₇-C₃₀ aralkyl, substituted or unsubstituted         C₁-C₁₀ alkoxy, substituted or unsubstituted C₆-C₃₀ aryloxy,         substituted or unsubstituted C₂-C₂₀ alkenyl, substituted or         unsubstituted C₃-C₃₀ silyl, substituted or unsubstituted C₆-C₃₀         aryl, substituted or unsubstituted C₃-C₃₀ heteroaryl,         substituted or unsubstituted C₃-C₃₀ arylsilyl, substituted or         unsubstituted C₀-C₂₀ amino, cyano, nitrile, isonitrile, and         phosphino; at least one of the R₃ and the R₄ is not hydrogen;     -   and the X, the Lb, and the Lc are defined the same as above.

More preferably, the A is CH or N.

More preferably, the A is N, and the R₃ substituent is located adjacent to the N.

Further preferably, the R₃ is D, C₁-C₄ alkyl, or C₁-C₄ alkyl including at least one D.

Most preferably, the R₃ is CD₃.

Preferably, the R₄ substituent is located adjacent or opposite to a metal Ir-carbon bond.

Preferably, the metal compound has one of the following structures:

-   -   where the R₁ and the R₂ have a maximum substitution number; the         R₁-R₂ are independently selected from hydrogen, substituted or         unsubstituted C₁-C₆ alkyl, substituted or unsubstituted C₃-C₆         cycloalkyl, substituted or unsubstituted C₇-C₂₀ aralkyl,         substituted or unsubstituted C₃-C₃₀ heteroaryl, or substituted         or unsubstituted C₆-C₃₀ aryl; at least one of the R₁ and the R₂         is not hydrogen;     -   the R₃ and the R₄ are independently selected from hydrogen,         substituted or unsubstituted C₁-C₆ alkyl, and substituted or         unsubstituted C₃-C₁₀ cycloalkyl; at least one of the R₃ and the         R₄ is not hydrogen;     -   the X is independently selected from O, S, Se, C(R)₂, Si(R)₂,         and NR; the R is independently selected from substituted or         unsubstituted C₁-C₁₀ alkyl or alkoxy, substituted or         unsubstituted C₃-C₃₀ cycloalkyl, and substituted or         unsubstituted C₆-C₃₀ aryl;     -   and the “substituted” refers to substitution with deuterium, F,         Cl, Br, or C₁-C₄ alkyl.

Preferably, the X is O, S, Se, NR, or C(R)₂; and the R is independently selected from substituted or unsubstituted C₁-C₈ alkyl.

Preferably, the La is independently selected from one of the following structural formulas, corresponding parts or complete deuterides thereof, or corresponding parts or complete fluorides thereof:

X = O La1   X = S La2   X = Se La3   X = C(CH₃)₂ La4   X = NCH₃ La5   X = N(i-Pr) La6  

X = O La7   X = S La8   X = Se La9   X = C(CH₃)₂ La10  X = NCH₃ La11  X = N(i-Pr) La12 

X = O La13  X = S La14  X = Se La15  X = C(CH₃)₂ La16  X = NCH₃ La17  X = N(i-Pr) La18 

X = O La19  X = S La20  X = Se La21  X = C(CH₃)₂ La22  X = NCH₃ La23  X = N(i-Pr) La24 

X = O La25  X = S La26  X = Se La27  X = C(CH₃)₂ La28  X = NCH₃ La29  X = N(i-Pr) La30 

X = O La31  X = S La32  X = Se La33  X = C(CH₃)₂ La34  X = NCH₃ La35  X = N(i-Pr) La36 

X = O La37  X = S La38  X = Se La39  X = C(CH₃)₂ La40  X = NCH₃ La41  X = N(i-Pr) La42 

X = O La43  X = S La44  X = Se La45  X = C(CH₃)₂ La46  X = NCH₃ La47  X = N(i-Pr) La48 

X = O La49  X = S La50  X = Se La51  X = C(CH₃)₂ La52  X = NCH₃ La53  X = N(i-Pr) La54 

X = O La55  X = S La56  X = Se La57  X = C(CH₃)₂ La58  X = NCH₃ La59  X = N(i-Pr) La60 

X = O La61  X = S La62  X = Se La63  X = C(CH₃)₂ La64  X = NCH₃ La65  X = N(i-Pr) La66 

X = O La67  X = S La68  X = Se La69  X = C(CH₃)₂ La70  X = NCH₃ La71  X = N(i-Pr) La72 

X = O La73  X = S La74  X = Se La75  X = C(CH₃)₂ La76  X = NCH₃ La77  X = N(i-Pr) La78 

X = O La79  X = S La80  X = Se La81  X = C(CH₃)₂ La82  X = NCH₃ La83  X = N(i-Pr) La84 

X = O La85  X = S La86  X = Se La87  X = C(CH₃)₂ La88  X = NCH₃ La89  X = N(i-Pr) La90 

X = O La91  X = S La92  X = Se La93  X = C(CH₃)₂ La94  X = NCH₃ La95  X = N(i-Pr) La96 

X = O La97  X = S La98  X = Se La99  X = C(CH₃)₂ La100  X = NCH₃ La101  X = N(i-Pr) La102 

X = O La103  X = S La104  X = Se La105  X = C(CH₃)₂ La106  X = NCH₃ La108  X = N(i-Pr) La107 

X = O La109  X = S La110  X = Se La111  X = C(CH₃)₂ La112  X = NCH₃ La113  X = N(i-Pr) La114 

X = O La115  X = S La116  X = Se La117  X = C(CH₃)₂ La118  X = NCH₃ La119  X = N(i-Pr) La120 

X = O La121  X = S La122  X = Se La123  X = C(CH₃)₂ La124  X = NCH₃ La125  X = N(i-Pr) La126 

X = O La127  X = S La128  X = Se La129  X = C(CH₃)₂ La130  X = NCH₃ La131  X = N(i-Pr) La132 

X = O La133  X = S La134  X = Se La135  X = C(CH₃)₂ La136  X = NCH₃ La137  X = N(i-Pr) La138 

X = O La139  X = S La140  X = Se La141  X = C(CH₃)₂ La142  X = NCH₃ La143  X = N(i-Pr) La144 

X = O La145  X = S La146  X = Se La147  X = C(CH₃)₂ La148  X = NCH₃ La149  X = N(i-Pr) La150 

X = O La151  X = S La152  X = Se La153  X = C(CH₃)₂ La154  X = NCH₃ La155  X = N(i-Pr) La156 

X = O La157  X = S La158  X = Se La159  X = C(CH₃)₂ La160  X = NCH₃ La161  X = N(i-Pr) La162 

X = O La163  X = S La164  X = Se La165  X = C(CH₃)₂ La166  X = NCH₃ La167  X = N(i-Pr) La168 

X = O La169  X = S La170  X = Se La171  X = C(CH₃)₂ La172  X = NCH₃ La173  X = N(i-Pr) La174 

X = O La175  X = S La176  X = Se La177  X = C(CH₃)₂ La178  X = NCH₃ La179  X = N(i-Pr) La180 

X = O La181  X = S La182  X = Se La183  X = C(CH₃)₂ La184  X = NCH₃ La 185  X = N(i-Pr) La186 

X = O La187  X = S La188  X = Se La189  X = C(CH₃)₂ La190  X = NCH₃ La191  X = N(i-Pr) La192 

X = O La193  X = S La194  X = Se La195  X = C(CH₃)₂ La196  X = NCH₃ La197  X = N(i-Pr) La198 

X = O La199  X = S La200  X = Se La201  X = C(CH₃)₂ La202  X = NCH₃ La203  X = N(i-Pr) La204 

X = O La205  X = S La206  X = Se La207  X = C(CH₃)₂ La208  X = NCH₃ La209  X = N(i-Pr) La210 

X = O La211  X = S La212  X = Se La213  X = C(CH₃)₂ La214  X = NCH₃ La215  X = N(i-Pr) La216 

X = O La217  X = S La218  X = Se La219  X = C(CH₃)₂ La220  X = NCH₃ La221  X = N(i-Pr) La222 

X = O La223  X = S La224  X = Se La225  X = C(CH₃)₂ La226  X = NCH₃ La227  X = N(i-Pr) La228 

X = O La229  X = S La230  X = Se La231  X = C(CH₃)₂ La232  X = NCH₃ La233  X = N(i-Pr) La234 

X = O La235  X = S La236  X = Se La237  X = C(CH₃)₂ La238  X = NCH₃ La239  X = N(i-Pr) La240 

X = O La241  X = S La242  X = Se La243  X = C(CH₃)₂ La244  X = NCH₃ La245  X = N(i-Pr) La246 

X = O La247  X = S La248  X = Se La249  X = C(CH₃)₂ La250  X = NCH₃ La251  X = N(i-Pr) La252 

X = O La253  X = S La254  X = Se La255  X = C(CH₃)₂ La256  X = NCH₃ La257  X = N(i-Pr) La258 

X = O La259  X = S La260  X = Se La261  X = C(CH₃)₂ La262  X = NCH₃ La263  X = N(i-Pr) La264 

X = O La265  X = S La266  X = Se La267  X = C(CH₃)₂ La268  X = NCH₃ La269  X = N(i-Pr) La270 

X = O La271  X = S La272  X = Se La273  X = C(CH₃)₂ La274  X = NCH₃ La275  X = N(i-Pr) La276 

X = O La277  X = S La278  X = Se La279  X = C(CH₃)₂ La280  X = NCH₃ La281  X = N(i-Pr) La282 

X = O La283  X = S La284  X = Se La285  X = C(CH₃)₂ La286  X = NCH₃ La287  X = N(i-Pr) La288 

X = O La289  X = S La290  X = Se La291  X = C(CH₃)₂ La292  X = NCH₃ La293  X = N(i-Pr) La294 

X = O La295  X = S La296  X = Se La297  X = C(CH₃)₂ La298  X = NCH₃ La299  X = N(i-Pr) La300 

X = O La301  X = S La302  X = Se La303  X = C(CH₃)₂ La304  X = NCH₃ La305  X = N(i-Pr) La306 

X = O La307  X = S La308  X = Se La309  X = C(CH₃)₂ La310  X = NCH₃ La311  X = N(i-Pr) La312 

X = O La313  X = S La314  X = Se La315  X = C(CH₃)₂ La316  X = NCH₃ La317  X = N(i-Pr) La318 

X = O La319  X = S La320  X = Se La321  X = C(CH₃)₂ La322  X = NCH₃ La323  X = N(i-Pr) La324 

X = O La325  X = S La326  X = Se La327  X = C(CH₃)₂ La328  X = NCH₃ La329  X = N(i-Pr) La330 

X = O La331  X = S La332  X = Se La333  X = C(CH₃)₂ La334  X = NCH₃ La335  X = N(i-Pr) La336 

X = O La337  X = S La338  X = Se La339  X = C(CH₃)₂ La340  X = NCH₃ La341  X = N(i-Pr) La342 

X = O La343  X = S La344  X = Se La345  X = C(CH₃)₂ La346  X = NCH₃ La347  X = N(i-Pr) La348 

X = O La349  X = S La350  X = Se La351  X = C(CH₃)₂ La352  X = NCH₃ La353  X = N(i-Pr) La354 

X = O La355  X = S La356  X = Se La357  X = C(CH₃)₂ La358  X = NCH₃ La359  X = N(i-Pr) La360 

X = O La361  X = S La362  X = Se La363  X = C(CH₃)₂ La364  X = NCH₃ La365  X = N(i-Pr) La366 

X = O La367  X = S La368  X = Se La369  X = C(CH₃)₂ La370  X = NCH₃ La371  X = N(i-Pr) La372 

X = O La373  X = S La374  X = Se La375  X = C(CH₃)₂ La376  X = NCH₃ La377  X = N(i-Pr) La378 

X = O La379  X = S La380  X = Se La381  X = C(CH₃)₂ La382  X = NCH₃ La383  X = N(i-Pr) La384 

X = O La385  X = S La386  X = Se La387  X = C(CH₃)₂ La388  X = NCH₃ La389  X = N(i-Pr) La390 

X = O La391  X = S La392  X = Se La393  X = C(CH₃)₂ La394  X = NCH₃ La395  X = N(i-Pr) La396 

X = O La397  X = S La398  X = Se La399  X = C(CH₃)₂ La400  X = NCH₃ La401  X = N(i-Pr) La402 

X = O La403  X = S La404  X = Se La405  X = C(CH₃)₂ La406  X = NCH₃ La407  X = N(i-Pr) La408 

X = O La409  X = S La410  X = Se La411  X = C(CH₃)₂ La412  X = NCH₃ La413  X = N(i-Pr) La414 

X = O La415  X = S La416  X = Se La417  X = C(CH₃)₂ La418  X = NCH₃ La419  X = N(i-Pr) La420 

X = O La421  X = S La422  X = Se La423  X = C(CH₃)₂ La424  X = NCH₃ La425  X = N(i-Pr) La426 

X = O La427  X = S La428  X = Se La429  X = C(CH₃)₂ La430  X = NCH₃ La431  X = N(i-Pr) La432 

X = O La433  X = S La434  X = Se La435  X = C(CH₃)₂ La436  X = NCH₃ La437  X = N(i-Pr) La438 

X = O La439  X = S La440  X = Se La441  X = C(CH₃)₂ La442  X = NCH₃ La443  X = N(i-Pr) La444 

X = O La445  X = S La446  X = Se La447  X = C(CH₃)₂ La448  X = NCH₃ La449  X = N(i-Pr) La450 

X = O La451  X = S La452  X = Se La453  X = C(CH₃)₂ La454  X = NCH₃ La455  X = N(i-Pr) La456 

X = O La457  X = S La458  X = Se La459  X = C(CH₃)₂ La460  X = NCH₃ La461  X = N(i-Pr) La462 

X = O La463  X = S La464  X = Se La465  X = C(CH₃)₂ La466  X = NCH₃ La467  X = N(i-Pr) La468 

X = O La469  X = S La470  X = Se La471  X = C(CH₃)₂ La472  X = NCH₃ La473  X = N(i-Pr) La474 

X = O La475  X = S La476  X = Se La477  X = C(CH₃)₂ La478  X = NCH₃ La479  X = N(i-Pr) La480 

X = O La481  X = S La482  X = Se La483  X = C(CH₃)₂ La484  X = NCH₃ La485  X = N(i-Pr) La486 

X = O La487  X = S La488  X = Se La489  X = C(CH₃)₂ La490  X = NCH₃ La491  X = N(i-Pr) La492 

X = O La493  X = S La494  X = Se La495  X = C(CH₃)₂ La496  X = NCH₃ La497  X = N(i-Pr) La498 

X = O La499  X = S La500  X = Se La501  X = C(CH₃)₂ La502  X = NCH₃ La503  X = N(i-Pr) La504 

X = O La505  X = S La506  X = Se La507  X = C(CH₃)₂ La508  X = NCH₃ La509  X = N(i-Pr) La510 

X = O La511  X = S La512  X = Se La513  X = C(CH₃)₂ La514  X = NCH₃ La515  X = N(i-Pr) La516 

X = O La517  X = S La518  X = Se La519  X = C(CH₃)₂ La520  X = NCH₃ La521  X = N(i-Pr) La522 

X = O La523  X = S La524  X = Se La525  X = C(CH₃)₂ La526  X = NCH₃ La527  X = N(i-Pr) La528 

X = O La529  X = S La530  X = Se La531  X = C(CH₃)₂ La532  X = NCH₃ La533  X = N(i-Pr) La534 

X = O La535  X = S La536  X = Se La537  X = C(CH₃)₂ La538  X = NCH₃ La539  X = N(i-Pr) La540 

X = O La541  X = S La542  X = Se La543  X = C(CH₃)₂ La544  X = NCH₃ La545  X = N(i-Pr) La546 

X = O La547  X = S La548  X = Se La549  X = C(CH₃)₂ La550  X = NCH₃ La551  X = N(i-Pr) La552 

X = O La553  X = S La554  X = Se La555  X = C(CH₃)₂ La556  X = NCH₃ La557  X = N(i-Pr) La558 

X = O La559  X = S La560  X = Se La561  X = C(CH₃)₂ La562  X = NCH₃ La563  X = N(i-Pr) La564 

X = O La565  X = S La566  X = Se La567  X = C(CH₃)₂ La568  X = NCH₃ La569  X = N(i-Pr) La570 

X = O La571  X = S La572  X = Se La573  X = C(CH₃)₂ La574  X = NCH₃ La575  X = N(i-Pr) La576 

X = O La577  X = S La578  X = Se La579  X = C(CH₃)₂ La580  X = NCH₃ La581  X = N(i-Pr) La582 

X = O La583  X = S La584  X = Se La585  X = C(CH₃)₂ La586  X = NCH₃ La587  X = N(i-Pr) La588 

X = O La589  X = S La590  X = Se La591  X = C(CH₃)₂ La592  X = NCH₃ La593  X = N(i-Pr) La594 

X = O La595  X = S La596  X = Se La597  X = C(CH₃)₂ La598  X = NCH₃ La599  X = N(i-Pr) La600 

X = O La601  X = S La602  X = Se La603  X = C(CH₃)₂ La604  X = NCH₃ La605  X = N(i-Pr) La606 

X = O La607  X = S La608  X = Se La609  X = C(CH₃)₂ La610  X = NCH₃ La611  X = N(i-Pr) La612 

X = O La613  X = S La614  X = Se La615  X = C(CH₃)₂ La616  X = NCH₃ La617  X = N(i-Pr) La618 

X = O La619  X = S La620  X = Se La621  X = C(CH₃)₂ La622  X = NCH₃ La623  X = N(i-Pr) La624 

X = O La625  X = S La626  X = Se La627  X = C(CH₃)₂ La628  X = NCH₃ La629  X = N(i-Pr) La630 

X = O La631  X = S La632  X = Se La633  X = C(CH₃)₂ La634  X = NCH₃ La635  X = N(i-Pr) La636 

X = O La637  X = S La638  X = Se La639  X = C(CH₃)₂ La640  X = NCH₃ La641  X = N(i-Pr) La642 

X = O La643  X = S La644  X = Se La645  X = C(CH₃)₂ La646  X = NCH₃ La647  X = N(i-Pr) La648 

X = O La649  X = S La650  X = Se La651  X = C(CH₃)₂ La652  X = NCH₃ La653  X = N(i-Pr) La654 

X = O La655  X = S La656  X = Se La657  X = C(CH₃)₂ La658  X = NCH₃ La659  X = N(i-Pr) La660 

X = O La661  X = S La662  X = Se La663  X = C(CH₃)₂ La664  X = NCH₃ La665  X = N(i-Pr) La666 

X = O La667  X = S La668  X = Se La669  X = C(CH₃)₂ La670  X = NCH₃ La671  X = N(i-Pr) La672 

X = O La673  X = S La674  X = Se La675  X = C(CH₃)₂ La676  X = NCH₃ La677  X = N(i-Pr) La678 

X = O La679  X = S La680  X = Se La681  X = C(CH₃)₂ La682  X = NCH₃ La683  X = N(i-Pr) La684 

X = O La685  X = S La686  X = Se La687  X = C(CH₃)₂ La688  X = NCH₃ La689  X = N(i-Pr) La690 

X = O La691  X = S La692  X = Se La693  X = C(CH₃)₂ La694  X = NCH₃ La695  X = N(i-Pr) La696 

X = O La697  X = S La698  X = Se La699  X = C(CH₃)₂ La700  X = NCH₃ La701  X = N(i-Pr) La702 

X = O La703  X = S La704  X = Se La705  X = C(CH₃)₂ La706  X = NCH₃ La707  X = N(i-Pr) La708 

X = O La709  X = S La710  X = Se La711  X = C(CH₃)₂ La712  X = NCH₃ La713  X = N(i-Pr) La714 

X = O La715  X = S La716  X = Se La717  X = C(CH₃)₂ La718  X = NCH₃ La719  X = N(i-Pr) La720 

X = O La721  X = S La722  X = Se La723  X = C(CH₃)₂ La724  X = NCH₃ La725  X = N(i-Pr) La726 

X = O La727  X = S La728  X = Se La729  X = C(CH₃)₂ La730  X = NCH₃ La731  X = N(i-Pr) La732 

X = O La733  X = S La734  X = Se La735  X = C(CH₃)₂ La736  X = NCH₃ La737  X = N(i-Pr) La738 

X = O La739  X = S La740  X = Se La741  X = C(CH₃)₂ La742  X = NCH₃ La743  X = N(i-Pr) La744 

X = O La745  X = S La746  X = Se La747  X = C(CH₃)₂ La748  X = NCH₃ La749  X = N(i-Pr) La750 

X = O La751  X = S La752  X = Se La753  X = C(CH₃)₂ La754  X = NCH₃ La755  X = N(i-Pr) La756 

X = O La757  X = S La758  X = Se La759  X = C(CH₃)₂ La760  X = NCH₃ La761  X = N(i-Pr) La762 

X = O La763  X = S La764  X = Se La765  X = C(CH₃)₂ La766  X = NCH₃ La767  X = N(i-Pr) La768 

X = O La769  X = S La770  X = Se La771  X = C(CH₃)₂ La772  X = NCH₃ La773  X = N(i-Pr) La774 

X = O La775  X = S La776  X = Se La777  X = C(CH₃)₂ La778  X = NCH₃ La779  X = N(i-Pr) La780 

X = O La781  X = S La782  X = Se La783  X = C(CH₃)₂ La784  X = NCH₃ La785  X = N(i-Pr) La786 

X = O La787  X = S La788  X = Se La789  X = C(CH₃)₂ La790  X = NCH₃ La791  X = N(i-Pr) La792 

X = O La793  X = S La794  X = Se La795  X = C(CH₃)₂ La796  X = NCH₃ La797  X = N(i-Pr) La798 

X = O La799  X = S La800  X = Se La801  X = C(CH₃)₂ La802  X = NCH₃ La803  X = N(i-Pr) La804 

X = O La805  X = S La806  X = Se La807  X = C(CH₃)₂ La808  X = NCH₃ La809  X = N(i-Pr) La810 

X = O La811  X = S La812  X = Se La813  X = C(CH₃)₂ La814  X = NCH₃ La815  X = N(i-Pr) La816 

X = O La817  X = S La818  X = Se La819  X = C(CH₃)₂ La820  X = NCH₃ La821  X = N(i-Pr) La822 

X = O La823  X = S La824  X = Se La825  X = C(CH₃)₂ La826  X = NCH₃ La827  X = N(i-Pr) La828 

X = O La829  X = S La830  X = Se La831  X = C(CH₃)₂ La832  X = NCH₃ La833  X = N(i-Pr) La834 

X = O La835  X = S La836  X = Se La837  X = C(CH₃)₂ La838  X = NCH₃ La839  X = N(i-Pr) La840 

X = O La841  X = S La842  X = Se La843  X = C(CH₃)₂ La844  X = NCH₃ La845  X = N(i-Pr) La846 

X = O La847  X = S La848  X = Se La849  X = C(CH₃)₂ La850  X = NCH₃ La851  X = N(i-Pr) La852 

X = O La853  X = S La854  X = Se La855  X = C(CH₃)₂ La856  X = NCH₃ La857  X = N(i-Pr) La858 

X = O La859  X = S La860  X = Se La861  X = C(CH₃)₂ La862  X = NCH₃ La863  X = N(i-Pr) La864 

X = O La865  X = S La866  X = Se La867  X = C(CH₃)₂ La868  X = NCH₃ La869  X = N(i-Pr) La870 

X = O La871  X = S La872  X = Se La873  X = C(CH₃)₂ La874  X = NCH₃ La875  X = N(i-Pr) La876 

X = O La877  X = S La878  X = Se La879  X = C(CH₃)₂ La880  X = NCH₃ La881  X = N(i-Pr) La882 

X = O La883  X = S La884  X = Se La885  X = C(CH₃)₂ La886  X = NCH₃ La887  X = N(i-Pr) La888 

X = O La889  X = S La890  X = Se La891  X = C(CH₃)₂ La892  X = NCH₃ La893  X = N(i-Pr) La894 

X = O La895  X = S La896  X = Se La897  X = C(CH₃)₂ La898  X = NCH₃ La899  X = N(i-Pr) La900 

X = O La901  X = S La902  X = Se La903  X = C(CH₃)₂ La904  X = NCH₃ La905  X = N(i-Pr) La906 

X = O La907  X = S La908v X = Se La909  X = C(CH₃)₂ La910  X = NCH₃ La911  X = N(i-Pr) La912 

X = O La913  X = S La914  X = Se La915  X = C(CH₃)₂ La916  X = NCH₃ La917  X = N(i-Pr) La918 

X = O La919  X = S La920  X = Se La921  X = C(CH₃)₂ La922  X = NCH₃ La923  X = N(i-Pr) La924 

X = O La925  X = S La926  X = Se La927  X = C(CH₃)₂ La928  X = NCH₃ La929  X = N(i-Pr) La930 

X = O La931  X = S La932  X = Se La933  X = C(CH₃)₂ La934  X = NCH₃ La935  X = N(i-Pr) La936 

X = O La937  X = S La938  X = Se La939  X = C(CH₃)₂ La940  X = NCH₃ La941  X = N(i-Pr) La942 

X = O La943  X = S La944  X = Se La945  X = C(CH₃)₂ La946  X = NCH₃ La947  X = N(i-Pr) La948 

X = O La949  X = S La950  X = Se La951  X = C(CH₃)₂ La952  X = NCH₃ La953  X = N(i-Pr) La954 

X = O La955  X = S La956  X = Se La957  X = C(CH₃)₂ La958  X = NCH₃ La959  X = N(i-Pr) La960 

X = O La961  X = S La962  X = Se La963  X = C(CH₃)₂ La964  X = NCH₃ La965  X = N(i-Pr) La966 

X = O La967  X = S La968  X = Se La969  X = C(CH₃)₂ La970  X = NCH₃ La971  X = N(i-Pr) La972 

X = O La973  X = S La974  X = Se La975  X = C(CH₃)₂ La976  X = NCH₃ La977  X = N(i-Pr) La978 

X = O La979  X = S La980  X = Se La981  X = C(CH₃)₂ La982  X = NCH₃ La983  X = N(i-Pr) La984 

X = O La985  X = S La986  X = Se La987  X = C(CH₃)₂ La988  X = NCH₃ La989  X = N(i-Pr) La990 

X = O La991  X = S La992  X = Se La993  X = C(CH₃)₂ La994  X = NCH₃ La995  X = N(i-Pr) La996 

X = O La997  X = S La998  X = Se La999  X = C(CH₃)₂ La1000 X = NCH₃ La1001 X = N(i-Pr) La1002

X = O La1003 X = S La1004 X = Se La1005 X = C(CH₃)₂ La1006 X = NCH₃ La1007 X = N(i-Pr) La1008

X = O La1009 X = S La1010 X = Se La1011 X = C(CH₃)₂ La1012 X = NCH₃ La1013 X = N(i-Pr) La1014

X = O La1015 X = S La1016 X = Se La1017 X = C(CH₃)₂ La1018 X = NCH₃ La1019 X = N(i-Pr) La1020

X = O La1021 X = S La1022 X = Se La1023 X = C(CH₃)₂ La1024 X = NCH₃ La1025 X = N(i-Pr) La1026

X = O La1027 X = S La1028 X = Se La1029 X = C(CH₃)₂ La1030 X = NCH₃ La1031 X = N(i-Pr) La1032

X = O La1033 X = S La1034 X = Se La1035 X = C(CH₃)₂ La1036 X = NCH₃ La1037 X = N(i-Pr) La1038

X = O La1039 X = S La1040 X = Se La1041 X = C(CH₃)₂ La1042 X = NCH₃ La1043 X = N(i-Pr) La1044

X = O La1045 X = S La1046 X = Se La1047 X = C(CH₃)₂ La1048 X = NCH₃ La1049 X = N(i-Pr) La1050

X = O La1051 X = S La1052 X = Se La1053 X = C(CH₃)₂ La1054 X = NCH₃ La1055 X = N(i-Pr) La1056

X = O La1057 X = S La1058 X = Se La1059 X = C(CH₃)₂ La1060 X = NCH₃ La1061 X = N(i-Pr) La1062

X = O La1063 X = S La1064 X = Se La1065 X = C(CH₃)₂ La1066 X = NCH₃ La1067 X = N(i-Pr) La1068

X = O La1069 X = S La1070 X = Se La1071 X = C(CH₃)₂ La1072 X = NCH₃ La1073 X = N(i-Pr) La1074

X = O La1075 X = S La1076 X = Se La1077 X = C(CH₃)₂ La1078 X = NCH₃ La1079 X = N(i-Pr) La1080

X = O La1081 X = S La1082 X = Se La1083 X = C(CH₃)₂ La1084 X = NCH₃ La1085 X = N(i-Pr) La1086

X = O La1087 X = S La1088 X = Se La1089 X = C(CH₃)₂ La1090 X = NCH₃ La1091 X = N(i-Pr) La1092

X = O La1093 X = S La1094 X = Se La1095 X = C(CH₃)₂ La1096 X = NCH₃ La1097 X = N(i-Pr) La1098

X = O La1099 X = S La1100 X = Se La1101 X = C(CH₃)₂ La1102 X = NCH₃ La1103 X = N(i-Pr) La1104

X = O La1105 X = S La1106 X = Se La1107 X = C(CH₃)₂ La1108 X = NCH₃ La1109 X = N(i-Pr) La1110

X = O La1111 X = S La1112 X = Se La1113 X = C(CH₃)₂ La1114 X = NCH₃ La1115 X = N(i-Pr) La1116

X = O La1117 X = S La1118 X = Se La1119 X = C(CH₃)₂ La1120 X = NCH₃ La1121 X = N(i-Pr) La1122

X = O La1123 X = S La1124 X = Se La1125 X = C(CH₃)₂ La1126 X = NCH₃ La1127 X = N(i-Pr) La1128

X = O La1129 X = S La1130 X = Se La1131 X = C(CH₃)₂ La1132 X = NCH₃ La1133 X = N(i-Pr) La1134

X = O La1135 X = S La1136 X = Se La1137 X = C(CH₃)₂ La1138 X = NCH₃ La1139 X = N(i-Pr) La1140

X = O La1141 X = S La1142 X = Se La1143 X = C(CH₃)₂ La1144 X = NCH₃ La1145 X = N(i-Pr) La1146

X = O La1147 X = S La1148 X = Se La1149 X = C(CH₃)₂ La1150 X = NCH₃ La1151 X = N(i-Pr) La1152

X = O La1153 X = S La1154 X = Se La1155 X = C(CH₃)₂ La1156 X = NCH₃ La1157 X = N(i-Pr) La1158

X = O La1159 X = S La1160 X = Se La1161 X = C(CH₃)₂ La1162 X = NCH₃ La1163 X = N(i-Pr) La1164

X = O La1165 X = S La1166 X = Se La1167 X = C(CH₃)₂ La1168 X = NCH₃ La1169 X = N(i-Pr) La1170

X = O La1171 X = S La1172 X = Se La1173 X = C(CH₃)₂ La1174 X = NCH₃ La1175 X = N(i-Pr) La1176

X = O La1177 X = S La1178 X = Se La1179 X = C(CH₃)₂ La1180 X = NCH₃ La1181 X = N(i-Pr) La1182

X = O La1183 X = S La1184 X = Se La1185 X = C(CH₃)₂ La1186 X = NCH₃ La1187 X = N(i-Pr) La1188

X = O La1189 X = S La1190 X = Se La1191 X = C(CH₃)₂ La1192 X = NCH₃ La1193 X = N(i-Pr) La1194

X = O La1195 X = S La1196 X = Se La1197 X = C(CH₃)₂ La1198 X = NCH₃ La1199 X = N(i-Pr) La1200

La1201

La1202

La1203

La1204

La1205

La1206

La1207

La1208

La1209

La1210

La1211

La1212

La1213

La1214

La1215

La1216

La1217

La1218

La1219

La1220

La1221

La1222

La1223

La1224

La1225

La1226

La1227

La1228

La1229

La1230

La1231

La1232

La1233

La1234

La1235

La1236

La1237

La1238

La1239

La1240

La1241

La1242

La1243

La1244

La1245

La1246

La 1247

La1248

La1249

La1250

La1251

La1252

La1253

La1254

La1255

La1256

La1257

La1258

La1259

La1260

La1261

La1262

La1263

La1264

La1265

La1266

La1267

La1268

La1269

La1270

La1271

La1272

La1273

La1274

La1275

La1276

La1277

La1278

La1279

La1280

La1281

La1282

La1283

La 1284

La1285

La1286

La1287

La1288

La1289

La1290

La1291

La1292

La1293

La1294

La1295

La1296

La1297

La1298

La1299

La1300

La1301

La1302

La1303

La1304

La1305

La1306

La1307

-   -   the Lb and the Lc are independently selected from any one of La1         to La1307 according to claim 10, corresponding parts or complete         deuterides thereof, or corresponding parts or complete fluorides         thereof; and the La, the Lb, and the Lc do not have a structure         of the same number.

The Lb and the Lc are independently selected from one of the following structural formulas (a) to (k):

-   -   where a dotted line refers to a bond connected to metal iridium;     -   the number of Ra, Rb, and Rc is a maximum substitution number;     -   the Ra, the Rb, and the Rc are independently selected from         hydrogen, deuterium, halogen, substituted or unsubstituted         C₁-C₂₀ alkyl, substituted or unsubstituted C₃-C₃₀ cycloalkyl,         substituted or unsubstituted C₁-C₃₀ heteroalkyl, substituted or         unsubstituted C₇-C₃₀ aralkyl, substituted or unsubstituted         C₁-C₂₀ alkoxy, substituted or unsubstituted C₆-C₃₀ aryloxy,         substituted or unsubstituted C₂-C₂₀ alkenyl, substituted or         unsubstituted C₃-C₃₀ silyl, substituted or unsubstituted C₆-C₃₀         aryl, substituted or unsubstituted C₃-C₃₀ heteroaryl,         substituted or unsubstituted C₃-C₃₀ arylsilyl, substituted or         unsubstituted C₀-C₂₀ amino, cyano, nitrile, isonitrile, and         phosphino; or two adjacent substituents are optionally connected         into a ring or fused structure;     -   the “substituted” refers to substitution with deuterium, F, Cl,         Br, C₁-C₁₀ alkyl, C₁-C₁₀ alkoxy, C₃-C₁₀ cycloalkyl, amino         substituted with C₁-C₁₀ alkyl, C₆-C₃₀ aryl, C₇-C₃₀ aralkyl,         cyano, nitrile, isonitrile, and phosphino;     -   and a heteroatom in the heteroalkyl or heteroaryl is at least         one of S, O, and N.

Preferably, the Lb and the Lc are independently selected from the following structural formulas, corresponding parts or complete deuterides thereof, or corresponding parts or complete fluorides thereof; and the Lb and the Lc are not a ligand of the same number.

An electroluminescent device includes a cathode, an anode, and organic layers arranged between the cathode and the anode. At least one of the organic layers includes the metal complex according to any one of claims 1 to 12.

Another one of the objectives of the present invention is to provide an electroluminescent device, in which the organic layers include a light-emitting layer, and the metal complex is used as a light-emitting material, especially a red light-emitting material.

Another one of the objectives of the present invention is to provide an electroluminescent device, in which the organic layers include a hole injection layer, and the metal complex is used as a hole injection material.

The material of the present invention has the advantages of low sublimation temperature, high optical and electrochemical stability, high color saturation, high luminescence efficiency, and long device service life. As a phosphorescent material, the material of the present invention can convert a triplet state into light, so that the luminescence efficiency of an organic electroluminescent device can be improved, and the energy consumption is reduced.

DETAILED DESCRIPTION OF EMBODIMENTS

The following embodiments are merely described to facilitate the understanding of the technical invention, and should not be considered as specific limitations of the present invention.

All raw materials, solvents and the like involved in the synthesis of compounds in the present invention were purchased from Alfa, Acros, and other suppliers known to persons skilled in the art.

Example 1 Synthesis of a Compound A1 Synthesis of Ligands L50 and La385

Synthesis of a Compound L50

A compound L1-1 (36.0 g, 155.3 mmol, 1.0 eq), a compound L1-2 (23.3 g, 155.3 mmol, 1.0 eq), potassium carbonate (42.9 g, 310.7 mmol, 2.0 eq), and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (1.02 g, 1.5 mmol, 0.01 eq) were put into a 1 L three-mouth flask, and toluene (360 ml), ethanol (96 ml), and deionized water (96 ml) were added under the replacement of vacuum and nitrogen for 3 times. A mixture obtained was heated to 80° C., and stirred for a reaction for 6 hours under the protection of nitrogen. According to monitoring by TLC (with a mixture of ethyl acetate and n-hexane at a ratio of 1:10 as a developing agent), the raw material L1-1 was almost consumed completely. Cooling was conducted to room temperature, and liquid separation was conducted. An organic phase was washed with water (3*180 ml). An aqueous phase was extracted with ethyl acetate (150 ml) for 1 time. Suction filtration was conducted with silica gel. Washing was conducted with ethyl acetate until no obvious product residue existed. Concentration was conducted to obtain a yellow viscous liquid. The liquid was separated by column chromatography (with a mixture of ethyl acetate and n-hexane at a ratio of 1:20 as an eluent), and then concentration and drying were conducted to obtain 41.2 g of a white sugar-like solid compound L50 with a yield of 87.8%. Mass spectrometry was as follows: 302.4 (M+H)

Synthesis of a Compound La385

A compound L1-1 (28.7 g, 123.8 mmol, 1.0 eq), a compound L1-3 (28.5 g, 126.3 mmol, 1.02 eq), K₂CO₃ (34.2 g, 247.7 mmol, 2.0 eq), and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (0.81 g, 1.24 mmol, 0.01 eq) were put into a 1 L three-mouth flask, and toluene (290 ml), ethanol (90 ml), and H₂O (90 ml) were added under the replacement of vacuum and nitrogen for 3 times. A mixture obtained was heated to 80° C., and stirred for a reaction for 3 hours under the protection of nitrogen. According to monitoring by TLC (with a mixture of ethyl acetate and n-hexane at a ratio of 1:8 as a developing agent), the raw material L1-1 was almost consumed completely. Cooling was conducted to room temperature, and liquid separation was conducted. An organic phase was washed with water (3*180 ml). An aqueous phase was extracted with ethyl acetate (150 ml) for 1 time. Suction filtration was conducted with silica gel. Washing was conducted with ethyl acetate until no obvious product residue existed. Concentration was conducted to obtain a yellow viscous liquid. The liquid was separated by column chromatography (with a mixture of ethyl acetate and n-hexane at a ratio of 1:20 as an eluent), and then concentration and drying were conducted to obtain 36.8 g of a white sugar-like solid compound La385 with a yield of 78.9%. Mass spectrometry was as follows: 378.4 (M+H)

Synthesis of a Compound A1

Synthesis of a Compound A1-1

The compound L50 (6.7 g, 22.2 mmol, 2.0 eq) and silver oxide (2.58 g, 11.1 mmol, 1.0 eq) were added into a 250 ml three-mouth flask, and then a 4 A molecular sieve (2.5 g) and dichloromethane (130 ml) were added, and stirred at room temperature for 2 hours under the replacement of vacuum and nitrogen for 3 times until a solution became a brownish black suspension. According to monitoring by TLC (with a mixture of ethyl acetate and n-hexane at a ratio of 1:8 as a developing agent), the raw material L50 was almost consumed completely. Then, chloro(1,5-cyclooctadiene)iridium dimer (7.47 g, 11.1 mmol, 1.0 eq) was added into the reaction solution, and continuously stirred at room temperature for 8 hours until the solution became brownish red. According to monitoring by TLC (with a mixture of ethyl acetate and n-hexane at a ratio of 1:3 as a developing agent), a reaction was stopped until a product with high polarity was produced. After filtration was conducted, a filter cake was washed with a small amount of dichloromethane, and a filtrate was collected, and concentrated to about 60 ml. N-hexane (100 ml) was added, and stirred for 1 hour until a solid was precipitated out. The solid was rinsed with a small amount of n-hexane, filtered, and then dried to obtain 12.9 g of an orange red solid compound A1-1 with a yield of 91.8%. Mass spectrometry was as follows: 635.2 (M+H)

Synthesis of a Compound A1-2

The compound A1-1 (4.2 g, 6.61 mmol, 1.0 eq), the compound La385 (7.48 g, 19.8 mmol, 3.0 eq), and 2-ethoxyethanol (63 ml) were added into a 250 ml three-mouth flask, heated to 120° C., and stirred for 16 hours under the replacement of vacuum and nitrogen for 3 times. According to monitoring by TLC (with a mixture of ethyl acetate and n-hexane at a ratio of 1:3 as a developing agent), the raw material A-1 was almost consumed completely. A reaction solution was cooled to room temperature, and methanol (63 ml) was added into the reaction solution, and continuously stirred for 2 hours. After filtration was conducted, a filter cake was washed with a small amount of methanol, and then dried to obtain 3.8 g of an orange red solid compound A1-2 with a yield of 53.2%. The obtained compound was directly used in the next step without purification.

Synthesis of a Compound A1

The compound A1-2 (5.18 g), a compound L5 (4.91 g, 23.1 mmol, 3.5 eq), sodium carbonate (3.5 g, 33.0 mmol, 5.0 eq), and 2-ethoxyethanol (103 ml) were added into a 250 ml three-mouth flask, heated to 40° C., and stirred for 16 hours under the replacement of vacuum and nitrogen for 3 times. According to monitoring by TLC (with a mixture of ethyl acetate and n-hexane at a ratio of 1:5 as a developing agent), the raw material A1-2 was almost consumed completely. Then, methanol (103 ml) was added into a reaction solution, and continuously stirred at room temperature for 1 hour. After filtration was conducted, a filter cake was rinsed with a small amount of methanol. A solid obtained was stirred in dichloromethane (150 ml) for dissolved clarification. After filtration was conducted with silica gel, a filter cake was rinsed with a small amount of dichloromethane. Deionized water was added into a filtrate obtained for washing for 3 times (80 ml/time). Liquid separation was conducted, and an organic phase was collected, and spin-dried. A crude product was recrystallized with tetrahydrofuran/methanol (1 g/7 v/10 v) for 3 times, and then dried to obtain 3.8 g of a red solid compound A1 with a yield of 53.2%. 3.8 g of the crude product A1 was sublimated and purified to obtain 2.78 g of a sublimated pure product A1 with a yield of 73.1%. Mass spectrometry was as follows: 1081.4 (M+H). 1H NMR (400 MHz, CDCl₃) δ 8.36 (d, J=15.0 Hz, 2H), 8.07 (d, J=2.9 Hz, 2H), 7.98 (dd, J=14.6, 3.4 Hz, 1H), 7.77 (d, J=15.0 Hz, 2H), 7.54 (dd, J=14.7, 3.4 Hz, 1H), 7.47 (dd, J=14.9, 3.0 Hz, 2H), 7.38 (tt, J=9.2, 4.5 Hz, 3H), 7.31 (td, J=14.8, 3.4 Hz, 2H), 6.92 (d, J=3.1 Hz, 2H), 2.32 (d, J=15.0 Hz, 9H), 2.02-1.82 (m, 4H), 1.81-1.55 (m, 12H), 1.42-1.15 (m, 8H), 1.11-0.97 (m, 5H), 0.94 (t, J=13.2 Hz, 12H).

Example 2 Synthesis of a Compound A2 Synthesis of ligands La193 and La769

Synthesis of a Compound La193

With reference to the synthesis process and post-treatment and purification methods of the compound La385, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 366.2 (M+H).

Synthesis of a Compound La769

With reference to the synthesis process and post-treatment and purification methods of the compound La385, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 414.5 (M+H).

Synthesis of a Compound A2

Synthesis of a Compound A2-1

With reference to the synthesis process and post-treatment and purification methods of the compound A1-1, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 712.3 (M+H).

Synthesis of a Compound A2-2

With reference to the synthesis process and post-treatment and purification methods of the compound A1-2, only the corresponding raw materials were required to be changed. The obtained compound was directly used in the next step without purification.

Synthesis of a Compound A2

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 2.95 g of a target compound A2 with a yield of 48.9% was obtained. 2.95 g of the crude product A2 was sublimated and purified to obtain 2.08 g of a sublimated pure product A2 with a yield of 70.5%. Mass spectrometry was as follows: 1181.4 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.38 (d, J=20.0 Hz, 2H), 7.98 (dd, 2H), 7.78 (m, J=5.0 Hz, 2H), 7.53 (d, J=15.0 Hz, 4H), 7.47 (m, 2H), 7.39 (m, 4H), 7.31 (m, 4H), 2.43 (d, 2H), 2.34 (s, 6H), 1.88 (m, 1H), 1.81 (m, J=7.2 Hz, 2H), 1.69 (m, J=37.5 Hz, 2H), 1.31 (m, 4H), 1.24 (m, 4H), 1.01 (m, J=5.7 Hz, 7H), 0.94 (m, 12H), 0.87 (d, 5H).

Example 3 Synthesis of a Compound A3

Synthesis of a Compound A3

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 3.11 g of a target compound A3 with a yield of 50.2% was obtained. 3.11 g of the crude product A3 was sublimated and purified to obtain 2.17 g of a sublimated pure product A3 with a yield of 69.7%. Mass spectrometry was as follows: 1193.5 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.38 (d, J=20.0 Hz, 2H), 7.94 (dd, 2H), 7.72 (m, J=5.0 Hz, 2H), 7.55 (d, J=15.0 Hz, 4H), 7.46 (m, 2H), 7.39 (m, 4H), 7.31 (m, 4H), 2.34 (s, 6H), 1.88 (m, 3H), 1.77 (t, J=18.8 Hz, 3H), 1.66 (m, J=2.2 Hz, 5H), 1.31 (m, 4H), 1.24 (m, 4H), 1.01 (m, J=5.7 Hz, 8H), 0.94 (m, 12H).

Example 4 Synthesis of a Compound A4 Synthesis of a Ligand La1306

Synthesis of a Compound La1306

With reference to the synthesis process and post-treatment and purification methods of the compound La385, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 406.4 (M+H).

Synthesis of a Compound A4

Synthesis of a Compound A4-1

With reference to the synthesis process and post-treatment and purification methods of the compound A1-2, only the corresponding raw materials were required to be changed. The obtained compound was directly used in the next step without purification.

Synthesis of a Compound A4

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 2.71 g of a target compound A4 with a yield of 47.7% was obtained. 2.71 g of the crude product A4 was sublimated and purified to obtain 1.95 g of a sublimated pure product A4 with a yield of 71.9%. Mass spectrometry was as follows: 1173.4 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.41 (d, J=20.0 Hz, 2H), 7.96 (dd, 2H), 7.75 (m, J=5.0 Hz, 2H), 7.56 (d, J=15.0 Hz, 4H), 7.47 (m, 2H), 7.40 (m, 4H), 7.33 (m, 4H), 2.63 (t, 2H), 2.43 (d, 1H), 2.34 (s, 6H), 1.85 (m, J=32.9 Hz, 2H), 1.31 (m, 4H), 1.24 (m, 4H), 1.01 (m, J=5.7 Hz, 5H), 0.94 (m, 12H), 0.87 (m, 6H).

Example 5 Synthesis of a Compound A5 Synthesis of a Ligand La1

Synthesis of a Compound La1

With reference to the synthesis process and post-treatment and purification methods of the compound La385, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 352.4 (M+H).

Synthesis of a Compound A5

Synthesis of a Compound A5-1

With reference to the synthesis process and post-treatment and purification methods of the compound A1-2, only the corresponding raw materials were required to be changed. The obtained compound was directly used in the next step without purification.

Synthesis of a Compound A5

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 2.88 g of a target compound A5 with a yield of 49.2% was obtained. 2.88 g of the crude product A5 was sublimated and purified to obtain 2.03 g of a sublimated pure product A5 with a yield of 70.4%. Mass spectrometry was as follows: 1135.5 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.36 (d, J=15.0 Hz, 2H), 8.07 (d, J=2.9 Hz, 2H), 7.98 (dd, J=14.6, 3.4 Hz, 1H), 7.77 (d, J=15.0 Hz, 2H), 7.54 (dd, J=14.7, 3.4 Hz, 1H), 7.47 (dd, J=14.9, 3.0 Hz, 2H), 7.38 (tt, J=9.2, 4.5 Hz, 3H), 7.31 (td, J=14.8, 3.4 Hz, 2H), 6.92 (d, J=3.1 Hz, 2H), 2.87 (m, J=6.5 Hz, 1H), 2.32 (d, J=15.0 Hz, 9H), 1.88 (m, 2H), 1.76 (m, 2H), 1.66 (m, J=2.2 Hz, 4H), 1.52 (m, J=30.0 Hz, 8H), 1.39 (m, 4H), 1.27 (d, J=30.0 Hz, 3H), 1.20 (m, 6H), 1.00 (m, 5H), 0.87 (s, 12H).

Example 6 Synthesis of a Compound A6 Synthesis of a Compound A6

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 3.61 g of a target compound A6 with a yield of 54.2% was obtained. 3.61 g of the crude product A6 was sublimated and purified to obtain 2.61 g of a sublimated pure product A6 with a yield of 72.0%. Mass spectrometry was as follows: 1121.5 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.36 (d, J=15.0 Hz, 2H), 8.07 (d, J=2.9 Hz, 2H), 7.98 (dd, J=14.6, 3.4 Hz, 1H), 7.77 (d, J=15.0 Hz, 2H), 7.54 (dd, J=14.7, 3.4 Hz, 1H), 7.47 (dd, J=14.9, 3.0 Hz, 2H), 7.38 (tt, J=9.2, 4.5 Hz, 3H), 7.31 (td, J=14.8, 3.4 Hz, 2H), 6.92 (d, J=3.1 Hz, 2H), 2.87 (m, 1H), 2.54 (d, 2H), 2.32 (d, J=15.0 Hz, 9H), 1.88 (d, J=5.4 Hz, 4H), 1.83-1.73 (m, 8H), 1.67 (m, J=16.1, 6.1 Hz, 10H), 1.31 (m, 4H), 1.20 (m, J=2.6 Hz, 8H), 1.11 (m, 2H), 1.01 (m, J=15.0 Hz, 6H).

Example 7 Synthesis of a Compound A7 Synthesis of a Ligand L221

Synthesis of a Compound L112

A compound L10-1 (14.2 g, 82.5 mmol, 1.0 eq), a compound L10-2 (25.5 g, 82.5 mmol, 1.0 eq), tripotassium phosphate (35.0 g, 165.0 mmol, 2.0 eq), tris(dibenzylideneacetone)dipalladium (1.51 g, 1.65 mmol, 0.02 eq), and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.36 g, 3.3 mmol, 0.04 eq) were put into a 500 ml three-mouth flask, and toluene (150 ml) and deionized water (30 ml) were added under the replacement of vacuum and nitrogen for 3 times. A mixture obtained was heated to reflux, and stirred for a reaction overnight under the protection of nitrogen. According to monitoring by TLC (with a mixture of ethyl acetate and n-hexane at a ratio of 1:5 as a developing agent), the raw material L10-2 was almost consumed completely. The mixture was cooled to room temperature. Liquid separation was conducted, and an organic phase was collected. An aqueous phase was extracted with ethyl acetate (60 ml) for 1 time. Organic phases were combined, and concentrated to obtain a yellow viscous liquid. The liquid was separated by column chromatography (with a mixture of ethyl acetate and n-hexane at a ratio of 1:15 as an eluent), and then concentration and drying were conducted to obtain 16.1 g of a white-like solid compound L112 with a yield of 71.5%. Mass spectrometry was as follows: 275.3 (M+H)

Synthesis of a Compound L221

The compound L112 (16.1 g, 58.6 mmol, 1.0 eq), sodium hydride (4.23 g, 176.0 mmol, 3.0 eq), and deuterated ethanol (160 ml) were added into a 500 ml three-mouth flask under the replacement of vacuum and nitrogen for 3 times. A mixture obtained was heated to reflux, and stirred for a reaction for 48 hours under the protection of nitrogen. Cooling was conducted to room temperature. Heavy water (100 ml) was added, and stirred for 0.5 hour. Dichloromethane (250 ml) was added for extraction twice. An organic phase in the lower layer was collected, and spin-dried. An aqueous phase was extracted with ethyl acetate (60 ml) for 1 time. Organic phases were combined, and concentrated to obtain a yellow viscous liquid. The liquid was separated by column chromatography (with a mixture of ethyl acetate and n-hexane at a ratio of 1:15 as an eluent), and then concentration and drying were conducted to obtain 10.1 g of a white-like solid compound L221 with a yield of 62.1%. Mass spectrometry was as follows: 278.3 (M+H)

Synthesis of a Compound A7

The compound A5-1 (8.2 g, 4.7 mmol, 1.0 eq) and dichloromethane (205 ml) were added into a 250 ml three-mouth flask for stirring and dissolution, and silver trifluoromethanesulfonate (2.66 g, 10.3 mmol, 2.2 eq) was dissolved in isopropanol (66.5 ml), and then dropped into the three-mouth flask under the atmosphere of nitrogen. A mixture obtained was stirred at room temperature for a reaction for 18 hours. A reaction suspension was filtered with diatomite to remove a silver salt. A filtrate was spin-dried to obtain an orange red solid, which was directly used in a reaction in the next step without purification. The solid obtained, the compound L221 (3.91 g, 14.1 mmol, 3.0 eq), and ethanol (117 ml) were added into a 250 ml clean three-mouth flask under the replacement of vacuum and nitrogen for 3 times. A mixture obtained was heated to reflux, and stirred overnight. According to monitoring by TLC (with a mixture of ethyl acetate and n-hexane at a ratio of 1:5 as a developing agent), a new product was produced. A reaction solution was cooled to room temperature. After filtration was conducted, a filter cake was rinsed with a small amount of ethanol. A solid obtained was stirred in dichloromethane (160 ml) for dissolved clarification. After filtration was conducted with silica gel, a filter cake was rinsed with a small amount of DCM. Deionized water was added into a filtrate obtained for washing for 3 times (80 ml/time). Liquid separation was conducted, and an organic phase was collected, and spin-dried. A crude product was recrystallized with tetrahydrofuran/methanol (1 g/8 v/15 v) for 4 times, and then dried to obtain 2.54 g of a red solid compound A7 with a yield of 48.3%. 2.54 g of the crude product A7 was sublimated and purified to obtain 1.49 g of a sublimated pure product A7 with a yield of 58.6%. Mass spectrometry was as follows: 1195.4 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.36 (d, 2H), 8.30 (d, J=0.6 Hz, 2H), 8.23 (s, 1H), 8.07 (d, 1H), 7.98 (dd, 1H), 7.84-7.67 (m, 4H), 7.56 (m, J=23.7 Hz, 2H), 7.46 (m, J=5.2 Hz, 3H), 7.39 (m, 2H), 7.35-7.23 (m, 4H), 7.01 (d, 1H), 6.92 (d, 1H), 2.87 (m, 1H), 2.34 (m, J=27.4, 17.4 Hz, 13H), 1.97 (m, J=6.9 Hz, 2H), 1.72 (m, J=28.4, 21.6 Hz, 6H), 1.20 (d, 3H).

Example 8 Synthesis of a compound A8 Synthesis of a Ligand La199

Synthesis of a Compound La199

With reference to the synthesis process and post-treatment and purification methods of the compound La385, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 380.5 (M+H).

Synthesis of a Compound A8

Synthesis of a Compound A8-1

With reference to the synthesis process and post-treatment and purification methods of the compound A1-1, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 714.2 (M+H).

Synthesis of a compound A8-2

With reference to the synthesis process and post-treatment and purification methods of the compound A1-2, only the corresponding raw materials were required to be changed. The obtained compound was directly used in the next step without purification.

Synthesis of a compound A8

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 3.77 g of a target compound A8 with a yield of 56.2% was obtained. 3.77 g of the crude product A8 was sublimated and purified to obtain 2.41 g of a sublimated pure product A8 with a yield of 63.9%. Mass spectrometry was as follows: 1195.5 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.37 (d, J=20.0 Hz, 2H), 7.95 (dd, 2H), 7.77 (m, J=5.0 Hz, 2H), 7.54 (d, J=15.0 Hz, 4H), 7.46 (m, 2H), 7.37 (m, 3H), 7.30 (m, 4H), 2.43 (d, 2H), 2.35 (d, J=10.0 Hz, 9H), 1.88 (m, 1H), 1.86-1.68 (m, 3H), 1.66 (m, 1H), 1.31 (m, 4H), 1.24 (m, 4H), 1.01 (m, J=5.7 Hz, 6H), 0.94 (m, 12H), 0.87 (d, 6H).

Example 9 Synthesis of a Compound A9 Synthesis of a Ligand La235

Synthesis of a Compound La235

With reference to the synthesis process and post-treatment and purification methods of the compound La385, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 380.5 (M+H).

Synthesis of a compound A9

Synthesis of a Compound A9-1

With reference to the synthesis process and post-treatment and purification methods of the compound A1-1, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 714.2 (M+H).

Synthesis of a Compound A9-2

With reference to the synthesis process and post-treatment and purification methods of the compound A1-2, only the corresponding raw materials were required to be changed. The obtained compound was directly used in the next step without purification.

Synthesis of a Compound A9

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 3.02 g of a target compound A9 with a yield of 49.7% was obtained. 3.02 g of the crude product A9 was sublimated and purified to obtain 2.15 g of a sublimated pure product A9 with a yield of 71.1%. Mass spectrometry was as follows: 1195.5 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.39 (d, J=20.0 Hz, 2H), 7.94 (dd, 2H), 7.75 (m, J=5.0 Hz, 2H), 7.53 (d, J=15.0 Hz, 4H), 7.45 (m, 2H), 7.36 (m, 4H), 7.32 (m, 3H), 2.69 (s, 3H), 2.43 (s, 2H), 2.34 (s, 6H), 1.88 (m, 1H), 1.86-1.68 (m, 3H), 1.66 (m, 1H), 1.31 (m, 4H), 1.24 (m, 4H), 1.01 (m, J=5.7 Hz, 6H), 0.94 (m, 12H), 0.87 (d, 6H).

Example 10 Synthesis of a Compound A10 Synthesis of a Ligand La457

With reference to the synthesis process and post-treatment and purification methods of the compound La385, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 468.6 (M+H).

Synthesis of a compound A10

Synthesis of a compound A10-1

With reference to the synthesis process and post-treatment and purification methods of the compound A1-2, only the corresponding raw materials were required to be changed. The obtained compound was directly used in the next step without purification.

Synthesis of a Compound A10

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 2.88 g of a target compound A10 with a yield of 42.1% was obtained. 2.88 g of the crude product A10 was sublimated and purified to obtain 1.77 g of a sublimated pure product A10 with a yield of 61.4%. Mass spectrometry was as follows: 1171.5 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.36 (d, 2H), 8.07 (d, 2H), 7.98 (dd, 3H), 7.83 (d, 1H), 7.77 (m, 1H), 7.54 (m, 2H), 7.47 (d, 2H), 7.39 (m, 2H), 7.31 (m, 2H), 7.15 (d, 2H), 6.92 (d, 2H), 2.32 (d, J=15.0 Hz, 12H), 1.88 (m, 4H), 1.76 (m, 4H), 1.66 (m, J=2.2 Hz, 7H), 1.31 (m, 4H), 1.24 (m, 4H), 1.01 (m, J=5.7 Hz, 5H), 0.94 (m, 12H).

Example 11 Synthesis of a Compound A11 Synthesis of a Ligand La397

With reference to the synthesis process and post-treatment and purification methods of the compound La385, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 420.6 (M+H).

Synthesis of a Compound A11

Synthesis of a Compound A11-1

With reference to the synthesis process and post-treatment and purification methods of the compound A1-2, only the corresponding raw materials were required to be changed. The obtained compound was directly used in the next step without purification.

Synthesis of a Compound A11

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 2.57 g of a target compound A11 with a yield of 40.6% was obtained. 2.57 g of the crude product A11 was sublimated and purified to obtain 1.65 g of a sublimated pure product A11 with a yield of 64.2%. Mass spectrometry was as follows: 1123.5 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.36 (d, 2H), 8.07 (d, 2H), 7.98 (dd, 2H), 7.77 (m, 2H), 7.50 (m, J=35.0 Hz, 2H), 7.35 (m, J=40.0 Hz, 4H), 6.92 (d, 2H), 2.87 (m, 1H), 2.32 (d, J=15.0 Hz, 9H), 1.88 (m, 4H), 1.82-1.55 (m, 12H), 1.27 (m, J=35.0 Hz, 7H), 1.17 (m, 6H), 1.08-1.02 (m, 2H), 1.01-0.89 (m, 16H).

Example 12 Synthesis of a Compound A12 Synthesis of a Ligand L144

With reference to the synthesis process and post-treatment and purification methods of the compound L50, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 317.4 (M+H).

Synthesis of a Compound A12

Synthesis of a Compound A3-1

With reference to the synthesis process and post-treatment and purification methods of the compound A1-1, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 714.2 (M+H).

Synthesis of a Compound A12-1

With reference to the synthesis process and post-treatment and purification methods of the compound A1-2, only the corresponding raw materials were required to be changed. The obtained compound was directly used in the next step without purification.

Synthesis of a Compound A12

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 2.93 g of a target compound A12 with a yield of 51.3% was obtained. 2.93 g of the crude product A12 was sublimated and purified to obtain 1.86 g of a sublimated pure product A12 with a yield of 63.4%. Mass spectrometry was as follows: 1196.4 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.36 (d, 2H), 7.98 (d, 2H), 7.77 (d, 2H), 7.65 (m, J=25.0 Hz, 3H), 7.50 (m, J=35.0 Hz, 3H), 7.35 (m, J=40.0 Hz, 1H), 6.92 (s, 2H), 2.44 (s, 9H), 2.32 (d, J=15.0 Hz, 9H), 1.88 (m, 4H), 1.69 (t, J=26.1 Hz, 12H), 1.27 (m, J=35.0 Hz, 8H), 1.10-0.86 (m, 17H).

Example 13 Synthesis of a Compound A13 Synthesis of a Ligand L222

With reference to the synthesis process and post-treatment and purification methods of the compound L50, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 224.3 (M+H).

Synthesis of a compound A13

Synthesis of a Compound A13-1

With reference to the synthesis process and post-treatment and purification methods of the compound A1-2, only the corresponding raw materials were required to be changed. The obtained compound was directly used in the next step without purification.

Synthesis of a Compound A13

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 2.76 g of a target compound A13 with a yield of 41.2% was obtained. 2.76 g of the crude product A13 was sublimated and purified to obtain 1.79 g of a sublimated pure product A13 with a yield of 64.8%. Mass spectrometry was as follows: 1003.3 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.13 (d, 2H), 8.07 (d, 2H), 7.98 (dd, 1H), 7.77 (d, 1H), 7.66 (m, 1H), 7.50 (m, J=35.0 Hz, 2H), 7.40 (m, J=15.0 Hz, 4H), 7.31 (m, 1H), 6.92 (d, 2H), 2.32 (d, J=15.0 Hz, 9H), 1.88 (m, 2H), 1.76 (m, 2H), 1.66 (m, J=2.2 Hz, 4H), 1.31 (m, 4H), 1.24 (m, 4H), 1.01 (m, J=5.7 Hz, 4H), 0.94 (m, 12H).

Example 14 Synthesis of a Compound A14 Synthesis of a Ligand L174

With reference to the synthesis process and post-treatment and purification methods of the compound L50, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 392.5 (M+H).

Synthesis of a compound A14

Synthesis of a Compound A14-1

With reference to the synthesis process and post-treatment and purification methods of the compound A1-1, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 741.4 (M+H).

Synthesis of a compound A14-2

With reference to the synthesis process and post-treatment and purification methods of the compound A1-2, only the corresponding raw materials were required to be changed. The obtained compound was directly used in the next step without purification.

Synthesis of a compound A14

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 2.67 g of a target compound A14 with a yield of 43.1% was obtained. 2.67 g of the crude product A14 was sublimated and purified to obtain 1.68 g of a sublimated pure product A14 with a yield of 62.9%. Mass spectrometry was as follows: 1213.6 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.32 (d, 2H), 8.07 (d, 2H), 7.98 (dd, 2H), 7.80 (dd, J=25.0 Hz, 2H), 7.51 (m, J=25.0 Hz, 4H), 7.35 (m, J=40.0 Hz, 3H), 7.16 (d, 2H), 6.92 (d, 2H), 2.87 (m, 1H), 2.32 (d, J=15.0 Hz, 12H), 1.88 (m, 4H), 1.76 (m, 4H), 1.66 (m, J=2.2 Hz, 8H), 1.27 (m, J=35.0 Hz, 8H), 1.17 (d, 6H), 1.01 (m, J=5.7 Hz, 5H), 0.94 (m, 12H).

Example 15 Synthesis of a Compound A15 Synthesis of a Compound A15

Synthesis of a Compound A15

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 2.71 g of a target compound A15 with a yield of 44.2% was obtained. 2.71 g of the crude product A15 was sublimated and purified to obtain 1.62 g of a sublimated pure product A15 with a yield of 59.7%. Mass spectrometry was as follows: 1109.5 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.36 (d, J=15.0 Hz, 2H), 8.07 (d, J=2.9 Hz, 2H), 7.98 (dd, J=14.6, 3.4 Hz, 1H), 7.77 (d, J=15.0 Hz, 2H), 7.54 (dd, J=14.7, 3.4 Hz, 1H), 7.47 (dd, J=14.9, 3.0 Hz, 2H), 7.38 (tt, J=9.2, 4.5 Hz, 3H), 7.31 (td, J=14.8, 3.4 Hz, 2H), 6.92 (d, J=3.1 Hz, 2H), 2.32 (d, J=15.0 Hz, 9H), 1.88 (m, 4H), 1.81-1.59 (m, 12H), 1.00 (m, J=5.0 Hz, 18H), 0.89 (m, 9H), 0.86 (t, J=3.5 Hz, 2H).

Example 16 Synthesis of a Compound A16 Synthesis of a Compound A16

Synthesis of a Compound A16

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 2.83 g of a target compound A16 with a yield of 43.9% was obtained. 2.83 g of the crude product A16 was sublimated and purified to obtain 1.82 g of a sublimated pure product A16 with a yield of 64.3%. Mass spectrometry was as follows: 1137.5 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.36 (d, J=15.0 Hz, 2H), 8.07 (d, J=2.9 Hz, 2H), 7.98 (dd, J=14.6, 3.4 Hz, 1H), 7.77 (d, J=15.0 Hz, 2H), 7.54 (dd, J=14.7, 3.4 Hz, 1H), 7.47 (dd, J=14.9, 3.0 Hz, 2H), 7.38 (tt, J=9.2, 4.5 Hz, 3H), 7.31 (td, J=14.8, 3.4 Hz, 2H), 6.92 (d, J=3.1 Hz, 2H), 2.32 (d, J=15.0 Hz, 9H), 1.88 (m, 4H), 1.76 (m, 4H), 1.66 (m, J=2.2 Hz, 8H), 1.00 (m, 15H), 0.89 (m, 18H).

Example 17 Synthesis of a Compound A17 Synthesis of a Ligand L65

With reference to the synthesis process and post-treatment and purification methods of the compound L50, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 290.4 (M+H).

Synthesis of a compound A17

Synthesis of a Compound A17-1

With reference to the synthesis process and post-treatment and purification methods of the compound A1-2, only the corresponding raw materials were required to be changed. The obtained compound was directly used in the next step without purification.

Synthesis of a compound A17

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 3.16 g of a target compound A17 with a yield of 46.1% was obtained. 3.16 g of the crude product A17 was sublimated and purified to obtain 2.23 g of a sublimated pure product A17 with a yield of 70.5%. Mass spectrometry was as follows: 1097.5 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.60 (d, 1H), 8.36 (d, 1H), 8.07 (d, 1H), 7.96 (m, J=15.0 Hz, 2H), 7.77 (dd, 2H), 7.66 (m, 2H), 7.50 (dd, J=35.0 Hz, 2H), 7.44-7.26 (m, 3H), 7.19 (dd, 2H), 6.92 (s, 1H), 2.47 (d, 2H), 2.32 (d, J=15.0 Hz, 9H), 1.88 (m, 2H), 1.78 (m, J=20.0 Hz, 3H), 1.66 (m, J=2.2 Hz, 4H), 1.00 (m, J=5.0 Hz, 16H), 0.88 (m, J=15.0 Hz, 18H).

Example 18 Synthesis of a Compound A18 Synthesis of a Ligand La493

With reference to the synthesis process and post-treatment and purification methods of the compound La385, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 434.6 (M+H).

Synthesis of a compound A18

Synthesis of a compound A18-1

With reference to the synthesis process and post-treatment and purification methods of the compound A1-1, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 768.4 (M+H).

Synthesis of a compound A18-2

With reference to the synthesis process and post-treatment and purification methods of the compound A1-2, only the corresponding raw materials were required to be changed. The obtained compound was directly used in the next step without purification.

Synthesis of a compound A18

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 3.41 g of a target compound A18 with a yield of 43.8% was obtained. 3.41 g of the crude product A18 was sublimated and purified to obtain 2.33 g of a sublimated pure product A18 with a yield of 68.3%. Mass spectrometry was as follows: 1153.6 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.60 (d, 1H), 8.07 (d, 1H), 7.96 (m, J=15.0 Hz, 2H), 7.89 (dd, 2H), 7.66 (t, 1H), 7.54 (dd, 2H), 7.42-7.27 (m, 4H), 7.19 (dd, 2H), 6.92 (d, 1H), 2.47 (d, 4H), 2.32 (d, J=15.0 Hz, 9H), 1.88 (m, 2H), 1.78 (m, J=20.0 Hz, 4H), 1.66 (m, J=2.2 Hz, 4H), 1.00 (m, J=5.0 Hz, 16H), 0.88 (m, J=15.0 Hz, 24H).

Example 19 Synthesis of a Compound A19 Synthesis of a Ligand La529

With reference to the synthesis process and post-treatment and purification methods of the compound La385, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 434.6 (M+H).

Synthesis of a compound A19

Synthesis of a compound A19

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 3.03 g of a target compound A19 with a yield of 41.4% was obtained. 3.03 g of the crude product A19 was sublimated and purified to obtain 1.83 g of a sublimated pure product A19 with a yield of 60.3%. Mass spectrometry was as follows: 1153.6 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.60 (d, 1H), 8.39 (d, 1H), 8.07 (d, 1H), 7.96 (m, J=15.0 Hz, 2H), 7.66 (m, 4H), 7.54 (dd, 2H), 7.44-7.24 (m, 3H), 7.21 (dd, 1H), 6.91 (d, 1H), 2.43 (d, 4H), 2.35 (d, J=15.0 Hz, 9H), 2.06-1.55 (m, 10H), 1.03 (m, J=5.0 Hz, 16H), 0.86 (m, J=15.0 Hz, 24H).

Example 20 Synthesis of a Compound A20 Synthesis of a Ligand La1267

With reference to the synthesis process and post-treatment and purification methods of the compound L112, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 393.5 (M+H).

Synthesis of a compound A20

Synthesis of a Compound A20-1

With reference to the synthesis process and post-treatment and purification methods of the compound A1-1, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 727.3 (M+H).

Synthesis of a Compound A20-2

With reference to the synthesis process and post-treatment and purification methods of the compound A1-2, only the corresponding raw materials were required to be changed. The obtained compound was directly used in the next step without purification.

Synthesis of a compound A20

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 2.96 g of a target compound A20 with a yield of 39.8% was obtained. 2.96 g of the crude product A20 was sublimated and purified to obtain 1.84 g of a sublimated pure product A20 with a yield of 62.1%. Mass spectrometry was as follows: 1112.5 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.60 (d, 2H), 8.36 (d, 2H), 8.07 (d, 2H), 7.95 (dd, 1H), 7.71 (m, J=55.0 Hz, 2H), 7.41 (m, J=60.0 Hz, 2H), 7.19 (dd, 2H), 7.01 (d, 1H), 6.92 (d, 1H), 2.68 (s, 3H), 2.47 (d, 2H), 2.32 (d, J=15.0 Hz, 9H), 1.99-1.56 (m, 9H), 1.00 (m, J=5.0 Hz, 16H), 0.94-0.80 (m, 18H).

Example 21 Synthesis of a Compound A21 Synthesis of a Ligand La1307

With reference to the synthesis process and post-treatment and purification methods of the compound L221, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 396.5 (M+H).

Synthesis of a compound A21

Synthesis of a Compound A21-1

With reference to the synthesis process and post-treatment and purification methods of the compound A1-1, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 730.3 (M+H).

Synthesis of a compound A21-2

With reference to the synthesis process and post-treatment and purification methods of the compound A1-2, only the corresponding raw materials were required to be changed. The obtained compound was directly used in the next step without purification.

Synthesis of a compound A21

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 2.53 g of a target compound A21 with a yield of 38.1% was obtained. 2.53 g of the crude product A21 was sublimated and purified to obtain 1.62 g of a sublimated pure product A21 with a yield of 64.0%. Mass spectrometry was as follows: 1115.5 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.62 (d, 2H), 8.35 (d, 2H), 8.10 (d, 2H), 7.94 (dd, 1H), 7.72 (m, J=55.0 Hz, 2H), 7.41 (m, J=60.0 Hz, 2H), 7.19 (dd, 2H), 7.01 (d, 1H), 6.92 (d, 1H), 2.47 (d, 2H), 2.32 (d, J=15.0 Hz, 9H), 1.99-1.56 (m, 9H), 1.00 (m, J=5.0 Hz, 16H), 0.94-0.80 (m, 18H).

Example 22 Synthesis of a Compound A22 Synthesis of a Ligand La386

With reference to the synthesis process and post-treatment and purification methods of the compound La385, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 394.5 (M+H).

Synthesis of a compound A22

Synthesis of a Compound A22-1

With reference to the synthesis process and post-treatment and purification methods of the compound A1-1, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 728.4 (M+H).

Synthesis of a compound A22-2

With reference to the synthesis process and post-treatment and purification methods of the compound A1-2, only the corresponding raw materials were required to be changed. The obtained compound was directly used in the next step without purification.

Synthesis of a Compound A22

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 2.66 g of a target compound A22 with a yield of 40.1% was obtained. 2.66 g of the crude product A22 was sublimated and purified to obtain 1.84 g of a sublimated pure product A22 with a yield of 69.1%. Mass spectrometry was as follows: 1113.5 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.60 (d, 1H), 8.45 (dd, 1H), 8.36 (dd, 1H), 8.07 (d, 1H), 7.95 (dd, 1H), 7.86 (dd, 1H), 7.77 (dd, 1H), 7.66 (m, 2H), 7.56 (m, 2H), 7.47 (m, 2H), 7.33 (m, J=20.0 Hz, 2H), 7.19 (dd, 1H), 6.92 (d, 1H), 2.47 (d, 2H), 2.32 (d, J=15.0 Hz, 9H), 1.88 (m, 2H), 1.78 (m, J=20.0 Hz, 3H), 1.66 (m, J=2.2 Hz, 4H), 1.00 (m, J=5.0 Hz, 16H), 0.88 (m, J=15.0 Hz, 18H).

Example 23 Synthesis of a Compound A23 Synthesis of a Ligand La387

With reference to the synthesis process and post-treatment and purification methods of the compound La385, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 441.4 (M+H).

Synthesis of a compound A23

Synthesis of a Compound A23-1

With reference to the synthesis process and post-treatment and purification methods of the compound A1-1, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 775.3 (M+H).

Synthesis of a compound A23-2

With reference to the synthesis process and post-treatment and purification methods of the compound A1-2, only the corresponding raw materials were required to be changed. The obtained compound was directly used in the next step without purification.

Synthesis of a compound A23

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 2.31 g of a target compound A23 with a yield of 36.1% was obtained. 2.31 g of the crude product A23 was sublimated and purified to obtain 1.38 g of a sublimated pure product A23 with a yield of 59.7%. Mass spectrometry was as follows: 1160.4 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.60 (d, 1H), 8.45 (dd, 1H), 8.36 (dd, 1H), 8.07 (d, 1H), 7.95 (dd, 1H), 7.86 (dd, 1H), 7.77 (dd, 2H), 7.66 (m, 2H), 7.58-7.38 (m, 3H), 7.35 (d, 2H), 7.19 (d, 1H), 6.92 (d, 1H), 2.47 (d, 2H), 2.32 (d, J=15.0 Hz, 9H), 1.88 (m, 2H), 1.78 (m, J=20.0 Hz, 3H), 1.66 (m, J=2.2 Hz, 4H), 1.00 (m, J=5.0 Hz, 16H), 0.88 (m, J=15.0 Hz, 18H).

Example 24 Synthesis of a Compound A24 Synthesis of a Ligand La388

With reference to the synthesis process and post-treatment and purification methods of the compound La385, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 441.4 (M+H).

Synthesis of a compound A24

Synthesis of a compound A24-1

With reference to the synthesis process and post-treatment and purification methods of the compound A1-1, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 738.4 (M+H).

Synthesis of a compound A24-2

With reference to the synthesis process and post-treatment and purification methods of the compound A1-2, only the corresponding raw materials were required to be changed. The obtained compound was directly used in the next step without purification.

Synthesis of a compound A24

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 2.41 g of a target compound A24 with a yield of 40.3% was obtained. 2.41 g of the crude product A24 was sublimated and purified to obtain 1.55 g of a sublimated pure product A24 with a yield of 64.3%. Mass spectrometry was as follows: 1123.5 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.60 (d, 1H), 8.36 (d, 1H), 8.07 (d, 1H), 7.92 (m, J=25.0 Hz, 3H), 7.77 (d, 2H), 7.66 (m, 3H), 7.47 (d, 2H), 7.35 (d, 2H), 7.19 (dd, 1H), 6.92 (d, 1H), 2.47 (d, 2H), 2.32 (d, J=15.0 Hz, 9H), 1.88 (m, 2H), 1.78 (m, J=20.0 Hz, 3H), 1.72-1.57 (m, 10H), 1.00 (m, J=5.0 Hz, 16H), 0.88 (m, J=15.0 Hz, 18H).

Example 25 Synthesis of a compound A25 Synthesis of a Ligand La389

With reference to the synthesis process and post-treatment and purification methods of the compound La385, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 391.5 (M+H).

Synthesis of a compound A25

Synthesis of a Compound A25-1

With reference to the synthesis process and post-treatment and purification methods of the compound A1-1, only the corresponding raw materials were required to be changed. Mass spectrometry was as follows: 725.5 (M+H).

Synthesis of a compound A25-2

With reference to the synthesis process and post-treatment and purification methods of the compound A1-2, only the corresponding raw materials were required to be changed. The obtained compound was directly used in the next step without purification.

Synthesis of a compound A25

With reference to the synthesis process and post-treatment and purification methods of the compound A1, only the corresponding raw materials were required to be changed, and 2.53 g of a target compound A25 with a yield of 38.1% was obtained. 2.53 g of the crude product A25 was sublimated and purified to obtain 1.72 g of a sublimated pure product A25 with a yield of 65.9%. Mass spectrometry was as follows: 1110.5 (M+H). ¹H NMR (400 MHz, CDCl₃) δ 8.60 (d, 1H), 8.52 (d, 1H), 8.35 (m, J=10.0 Hz, 2H), 8.07 (d, 1H), 7.95 (dd, 2H), 7.77 (d, 2H), 7.66 (m, 2H), 7.52-7.31 (m, 3H), 7.16 (m, J=25.0 Hz, 2H), 6.92 (d, 1H), 3.82 (s, 3H), 2.47 (d, 2H), 2.32 (d, J=15.0 Hz, 9H), 1.88 (m, 2H), 1.78 (m, J=20.0 Hz, 3H), 1.66 (m, J=2.2 Hz, 4H), 1.00 (m, J=5.0 Hz, 15H), 0.88 (m, J=15.0 Hz, 18H).

Other compounds can be synthesized and sublimated by using corresponding materials according to same or similar methods.

Application Example: Manufacture of an organic electroluminescent device

A glass substrate with a size of 50 mm*50 mm*1.0 mm including an ITO (100 nm) transparent electrode was ultrasonically cleaned in ethanol for 10 minutes, dried at 150° C., and then treated with N₂ plasma for 30 minutes. The washed glass substrate was installed on a substrate support of a vacuum evaporation device. At first, a compound HATCN for covering the transparent electrode was evaporated on the surface of the side having a transparent electrode line to form a thin film with a thickness of 5 nm. Next, a layer of HTM1 was evaporated to form a thin film with a thickness of 60 nm. Then, a layer of HTM2 was evaporated on the HTM1 thin film to form a thin film with a thickness of 10 nm. After that, a main material CBP and a doping compound (including a reference compound X and a compound AX of the present invention) were co-evaporated on the HTM2 film layer to obtain a film with a thickness of 30 nm, where a ratio of the main material to the doping material was 90%:10%. An electron transport layer (ETL) film layer (25 nm) and a LiQ film layer (1 nm) was evaporated on a light-emitting layer in sequence. At last, a layer of A1 (100 nm) was evaporated to serve as an electrode.

Evaluation

Properties of a device obtained above were tested. In various examples and comparative examples, a constant-current power supply (Keithley 2400) was used, a current at a fixed density was used for flowing through light-emitting elements, and a spectroradiometer (CS 2000) was used for testing the light-emitting spectrum. Meanwhile, the voltage value was measured, and the time (LT90) when the brightness was reduced to 90% of an initial brightness was tested. Results are shown as follows.

Starting Current Peak LT90@ Doping voltage efficiency wavelength 3000 material V Cd/A nm nits Example 1 A1 4.11 28 614 221 Example 2 A2 4.13 30 615 244 Example 3 A3 4.09 35 615 246 Example 4 A4 4.08 32 616 228 Example 5 A5 4.10 31 615 249 Example 6 A6 4.11 29 614 238 Example 7 A7 4.13 28 615 332 Example 8 A8 4.10 34 616 301 Example 9 A9 4.09 35 616 355 Example 10 A10 4.12 31 615 281 Example 11 A11 4.10 29 615 279 Example 12 A12 4.08 31 615 211 Example 13 A13 4.08 27 614 184 Example 14 A14 4.07 29 615 209 Example 15 A15 4.09 29 615 239 Example 16 A16 4.10 29 615 268 Example 17 A17 4.11 30 615 298 Example 18 A18 4.12 31 615 288 Example 19 A19 4.13 30 615 264 Example 20 A20 4.10 31 615 269 Example 21 A21 4.09 31 615 333 Example 22 A22 4.10 31 615 268 Example 23 A23 4.12 30 616 256 Example 24 A24 4.10 30 615 262 Example 25 A25 4.09 31 615 228 Comparative Reference 4.21 21 610 108 Example 1 compound 1 Comparative Reference 4.18 20 612 120 Example 2 compound 2 Comparative Reference 4.25 21 611 98 Example 3 compound 3 Comparative Reference 4.28 19 608 86 Example 4 compound 4

Through comparison of the data in the above table, it can be seen that compared with reference compounds, the compound of the present invention used as a dopant in an organic electroluminescent device has the advantages that more excellent properties, such as driving voltage, luminescence efficiency, and device service life, are achieved.

According to the above results, it is indicated that the compound of the present invention has the advantages of high optical and electrochemical stability, high color saturation, high luminescence efficiency, and long service life, and can be used in organic electroluminescent devices. In particular, the metal complex has the potential for application in the OLED industry as a red light-emitting dopant. 

1. A metal complex, having a general formula of Ir(La)(Lb)(Lc), and comprising a ligand La as shown in the following formula (1),

wherein among A₁-A₄, one group is a C—C bond connected to an E ring, one group is a C-metal bond connected to a metal, one group is CR₄, and the other group is CR₀ or N; among A₅-A₈, one group is CR₃, and the other three groups independently refer to CR₀ or N; the number of R₁-R₂ is a maximum substitution number; R₀-R₄ are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C₁-C₁₀ alkyl, substituted or unsubstituted C₃-C₂₀ cycloalkyl, substituted or unsubstituted C₁-C₁₀ heteroalkyl, substituted or unsubstituted C₇-C₃₀ aralkyl, substituted or unsubstituted C₁-C₁₀ alkoxy, substituted or unsubstituted C₆-C₃₀ aryloxy, substituted or unsubstituted C₂-C₂₀ alkenyl, substituted or unsubstituted C₃-C₃₀ silyl, substituted or unsubstituted C₆-C₃₀ aryl, substituted or unsubstituted C₃-C₃₀ heteroaryl, substituted or unsubstituted C₃-C₃₀ arylsilyl, substituted or unsubstituted C₀-C₂₀ amino, cyano, nitrile, isonitrile, and phosphino; at least one of R₃ and R₄ is not hydrogen; when A₇ is CR₀, R₀ is not F; X is independently selected from O, S, Se, C(R)₂, Si(R)₂, NR, BR, and POR; the R is independently selected from substituted or unsubstituted C₁-C₁₀ alkyl or alkoxy, substituted or unsubstituted C₂-C₃₀ cycloalkyl, substituted or unsubstituted C₆-C₃₀ aryl, and substituted or unsubstituted C₁-C₁₈ heteroaryl; the “substituted” refers to substitution with deuterium, F, Cl, Br, C₁-C₄ alkyl, C₁-C₄ alkoxy, C₃-C₆ cycloalkyl, amino substituted with C₁-C₄ alkyl, cyano, nitrile, isonitrile, and phosphino; a heteroatom in the heteroalkyl or heteroaryl is at least one of S, O, and N; a dotted line refers to a bond connected to metal iridium; La, Lb, and Lc are different from each other, and any two of the three groups are connected to form a multidentate ligand, or the three groups are connected by a group; both the Lb and the Lc are a monoanionic bidentate ligand; and the “different from each other” refers to having different parent nucleus structures, having a same parent nucleus structure with different substituents, or having a same parent nucleus structure with a same substituent at different positions.
 2. The metal complex according to claim 1, having a structure as shown in the following formula (2):

wherein the A is CR₀ or N; the R₀-R₄ are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C₁-C₁₀ alkyl, substituted or unsubstituted C₃-C₂₀ cycloalkyl, substituted or unsubstituted C₁-C₁₀ heteroalkyl, substituted or unsubstituted C₇-C₃₀ aralkyl, substituted or unsubstituted C₁-C₁₀ alkoxy, substituted or unsubstituted C₆-C₃₀ aryloxy, substituted or unsubstituted C₂-C₂₀ alkenyl, substituted or unsubstituted C₃-C₃₀ silyl, substituted or unsubstituted C₆-C₃₀ aryl, substituted or unsubstituted C₃-C₃₀ heteroaryl, substituted or unsubstituted C₃-C₃₀ arylsilyl, substituted or unsubstituted C₀-C₂₀ amino, cyano, nitrile, isonitrile, and phosphino; at least one of the R₃ and the R₄ is not hydrogen; and the X, the Lb, and the Lc are defined the same as above.
 3. The metal complex according to claim 2, wherein the A is CH or N.
 4. The metal complex according to claim 3, wherein the A is N, and the R₃ substituent is located adjacent to the N.
 5. The metal complex according to claim 4, wherein the R₃ is D, C₁-C₄ alkyl, or C₁-C₄ alkyl including at least one D.
 6. The metal complex according to claim 5, wherein the R₃ is CD₃.
 7. The metal complex according to claim 2, wherein the R₄ substituent is located adjacent or opposite to a metal Ir-carbon bond.
 8. The metal complex according to claim 2, having one of the following structures:

wherein the R₁ and the R₂ have a maximum substitution number; the R₁-R₂ are independently selected from hydrogen, substituted or unsubstituted C₁-C₆ alkyl, substituted or unsubstituted C₃-C₆ cycloalkyl, substituted or unsubstituted C₇-C₂₀ aralkyl, substituted or unsubstituted C₃-C₃₀ heteroaryl, or substituted or unsubstituted C₆-C₃₀ aryl; at least one of the R₁ and the R₂ is not hydrogen; the R₃ and the R₄ are independently selected from hydrogen, substituted or unsubstituted C₁-C₆ alkyl, and substituted or unsubstituted C₃-C₁₀ cycloalkyl; at least one of the R₃ and the R₄ is not hydrogen; the X is independently selected from O, S, Se, C(R)₂, Si(R)₂, and NR; the R is independently selected from substituted or unsubstituted C₁-C₁₀ alkyl or alkoxy, substituted or unsubstituted C₃-C₃₀ cycloalkyl, and substituted or unsubstituted C₆-C₃₀ aryl; and the “substituted” refers to substitution with deuterium, F, Cl, Br, or C₁-C₄ alkyl.
 9. The metal complex according to claims 1 to 8, wherein the X is O, S, Se, NR, or C(R)₂; and the R is independently selected from substituted or unsubstituted C₁-C₈ alkyl.
 10. The metal complex according to claim 1, wherein the La is independently selected from one of the following structural formulas, corresponding parts or complete deuterides thereof, or corresponding parts or complete fluorides thereof;

X = O La1 X = S La2 X = Se La3 X = C(CH₃)₂ La4 X = NCH₃ La5 X = N(i-Pr) La6

X = O La7 X = S La8 X = Se La9 X = C(CH₃)₂ La10 X = NCH₃ La11 X = N(i-Pr) La12

X = O La13 X = S La14 X = Se La15 X = C(CH₃)₂ La16 X = NCH₃ La17 X = N(i-Pr) La18

X = O La19 X = S La20 X = Se La21 X = C(CH₃)₂ La22 X = NCH₃ La23 X = N-(i-Pr) La24

X = O La25 X = S La26 X = Se La27 X = C(CH₃)₂ La28 X = NCH₃ La29 X = N(i-Pr) La30

X = O La31 X = S La32 X = Se La33 X = C(CH₃)₂ La34 X = NCH₃ La35 X = N(i-Pr) La36

X = O La37 X = S La38 X = Se La39 X = C(CH₃)₂ La40 X = NCH₃ La41 X = N(i-Pr) La42

X = O La43 X = S La44 X = Se La45 X = C(CH₃)₂ La46 X = NCH₃ La47 X = N(i-Pr) La48

X = O La49 X = S La50 X = Se La51 X = C(CH₃)₂ La52 X = NCH₃ La53 X = N(i-Pr) La54

X = O La55 X = S La56 X = Se La57 X = C(CH₃)₂ La58 X = NCH₃ La59 X = N(i-Pr) La60

X = O La61 X = S La62 X = Se La63 X = C(CH₃)₂ La64 X = NCH₃ La65 X = N(i-Pr) La66

X = O La67 X = S La68 X = Se La69 X = C(CH₃)₂ La70 X = NCH₃ La71 X = N(i-Pr) La72

X = O La73 X = S La74 X = Se La75 X = C(CH₃)₂ La76 X = NCH₃ La77 X = N(i-Pr) La78

X = O La79 X = S La80 X = Se La81 X = C(CH₃)₂ La82 X = NCH₃ La83 X = N(i-Pr) La84

X = O La85 X = S La86 X = Se La87 X = C(CH₃)₂ La88 X = NCH₃ La89 X = N(i-Pr) La90

X = O La91 X = S La92 X = Se La93 X = C(CH₃)₂ La94 X = NCH₃ La95 X = N(i-Pr) La96

X = O La97 X = S La98 X = Se La99 X = C(CH₃)₂ La100 X = NCH₃ La101 X = N(i-Pr) La102

X = O La103 X = S La104 X = Se La105 X = C(CH₃)₂ La106 X = NCH₃ La107 X = N(i-Pr) La108

X = O La109 X = S La110 X = Se La111 X = C(CH₃)₂ La112 X = NCH₃ La113 X = N(i-Pr) La114

X = O La115 X = S La116 X = Se La117 X = C(CH₃)₂ La118 X = NCH₃ La119 X = N(i-Pr) La120

X = O La121 X = S La122 X = Se La123 X = C(CH₃)₂ La124 X = NCH₃ La125 X = N(i-Pr) La126

X = O La127 X = S La128 X = Se La129 X = C(CH₃)₂ La130 X = NCH₃ La131 X = N(i-Pr) La132

X = O La133 X = S La134 X = Se La135 X = C(CH₃)₂ La136 X = NCH₃ La137 X = N(i-Pr) La138

X = O La139 X = S La140 X = Se La141 X = C(CH₃)₂ La142 X = NCH₃ La143 X = N(i-Pr) La144

X = O La145 X = S La146 X = Se La147 X = C(CH₃)₂ La148 X = NCH₃ La149 X = N(i-Pr) La150

X = O La151 X = S La152 X = Se La153 X = C(CH₃)₂ La154 X = NCH₃ La155 X = N(i-Pr) La156

X = O La157 X = S La158 X = Se La159 X = C(CH₃)₂ La160 X = NCH₃ La161 X = N(i-Pr) La162

X = O La163 X = S La164 X = Se La165 X = C(CH₃)₂ La166 X = NCH₃ La167 X = N(i-Pr) La168

X = O La169 X = S La170 X = Se La171 X = C(CH₃)₂ La172 X = NCH₃ La173 X = N(i-Pr) La174

X = O La175 X = S La176 X = Se La177 X = C(CH₃)₂ La178 X = NCH₃ La179 X = N(i-Pr) La180

X = O La181 X = S La182 X = Se La183 X = C(CH₃)₂ La184 X = NCH₃ La185 X = N(i-Pr) La186

X = O La187 X = S La188 X = Se La189 X = C(CH₃)₂ La190 X = NCH₃ La191 X = N(i-Pr) La192

X = O La193 X = S La194 X = Se La195 X = C(CH₃)₂ La196 X = NCH₃ La197 X = N(i-Pr) La198

X = O La199 X = S La200 X = Se La201 X = C(CH₃)₂ La202 X = NCH₃ La203 X = N(i-Pr) La204

X = O La205 X = S La206 X = Se La207 X = C(CH₃)₂ La208 X = NCH₃ La209 X = N(i-Pr) La210

X = O La211 X = S La212 X = Se La213 X = C(CH₃)₂ La214 X = NCH₃ La215 X = N(i-Pr) La216

X = O La217 X = S La218 X = Se La219 X = C(CH₃)₂ La220 X = NCH₃ La221 X = N(i-Pr) La222

X = O La223 X = S La224 X = Se La225 X = C(CH₃)₂ La226 X = NCH₃ La227 X = N(i-Pr) La228

X = O La229 X = S La230 X = Se La231 X = C(CH₃)₂ La232 X = NCH₃ La233 X = N(i-Pr) La234

X = O La235 X = S La236 X = Se La237 X = C(CH₃)₂ La238 X = NCH₃ La239 X = N(i-Pr) La240

X = O La241 X = S La242 X = Se La243 X = C(CH₃)₂ La244 X = NCH₃ La245 X = N(i-Pr) La246

X = O La247 X = S La248 X = Se La249 X = C(CH₃)₂ La250 X = NCH₃ La251 X = N(i-Pr) La252

X = O La253 X = S La254 X = Se La255 X = C(CH₃)₂ La256 X = NCH₃ La257 X = N(i-Pr) La258

X = O La259 X = S La260 X = Se La261 X = C(CH₃)₂ La262 X = NCH₃ La263 X = N(i-Pr) La264

X = O La265 X = S La266 X = Se La267 X = C(CH₃)₂ La268 X = NCH₃ La269 X = N(i-Pr) La270

X = O La271 X = S La272 X = Se La273 X = C(CH₃)₂ La274 X = NCH₃ La275 X = N(i-Pr) La276

X = O La277 X = S La278 X = Se La279 X = C(CH₃)₂ La280 X = NCH₃ La281 X = N(i-Pr) La282

X = O La283 X = S La284 X = Se La285 X = C(CH₃)₂ La286 X = NCH₃ La287 X = N(i-Pr) La288

X = O La289 X = S La290 X = Se La291 X = C(CH₃)₂ La292 X = NCH₃ La293 X = N(i-Pr) La294

X = O La295 X = S La296 X = Se La297 X = C(CH₃)₂ La298 X = NCH₃ La299 X = N(i-Pr) La300

X = O La301 X = S La302 X = Se La303 X = C(CH₃)₂ La304 X = NCH₃ La305 X = N(i-Pr) La306

X = O La307 X = S La308 X = Se La309 X = C(CH₃)₂ La310 X = NCH₃ La311 X = N(i-Pr) La312

X = O La313 X = S La314 X = Se La315 X = C(CH₃)₂ La316 X = NCH₃ La317 X = N(i-Pr) La318

X = O La319 X = S La320 X = Se La321 X = C(CH₃)₂ La322 X = NCH₃ La323 X = N(i-Pr) La324

X = O La325 X = S La326 X = Se La327 X = C(CH₃)₂ La328 X = NCH₃ La329 X = N(i-Pr) La330

X = O La331 X = S La332 X = Se La333 X = C(CH₃)₂ La334 X = NCH₃ La335 X = N(i-Pr) La336

X = O La337 X = S La338 X = Se La339 X = C(CH₃)₂ La340 X = NCH₃ La341 X = N(i-Pr) La342

X = O La343 X = S La344 X = Se La345 X = C(CH₃)₂ La346 X = NCH₃ La347 X = N(i-Pr) La348

X = O La349 X = S La350 X = Se La351 X = C(CH₃)₂ La352 X = NCH₃ La353 X = N(i-Pr) La354

X = O La355 X = S La356 X = Se La357 X = C(CH₃)₂ La358 X = NCH₃ La359 X = N(i-Pr) La360

X = O La361 X = S La362 X = Se La363 X = C(CH₃)₂ La364 X = NCH₃ La365 X = N(i-Pr) La366

X = O La367 X = S La368 X = Se La369 X = C(CH₃)₂ La370 X = NCH₃ La371 X = N(i-Pr) La372

X = O La73 X = S La374 X = Se La375 X = C(CH₃)₂ La376 X = NCH₃ La377 X = N(i-Pr) La378

X = O La379 X = S La380 X = Se La381 X = C(CH₃)₂ La382 X = NCH₃ La383 X = N(i-Pr) La384

X = O La385 X = S La386 X = Se La387 X = C(CH₃)₂ La388 X = NCH₃ La389 X = N(i-Pr) La390

X = O La391 X = S La392 X = Se La393 X = C(CH₃)₂ La394 X = NCH₃ La395 X = N(i-Pr) La396

X = O La397 X = S La398 X = Se La399 X = C(CH₃)₂ La400 X = NCH₃ La401 X = N(i-Pr) La402

X = O La403 X = S La404 X = Se La405 X = C(CH₃)₂ La406 X = NCH₃ La407 X = N(i-Pr) La408

X = O La409 X = S La410 X = Se La411 X = C(CH₃)₂ La412 X = NCH₃ La413 X = N(i-Pr) La414

X = O La415 X = S La416 X = Se La417 X = C(CH₃)₂ La418 X = NCH₃ La419 X = N(i-Pr) La420

X = O La421 X = S La422 X = Se La423 X = C(CH₃)₂ La424 X = NCH₃ La425 X = N(i-Pr) La426

X = O La427 X = S La428 X = Se La429 X = C(CH₃)₂ La430 X = NCH₃ La431 X = N(i-Pr) La432

X = O La433 X = S La434 X = Se La435 X = C(CH₃)₂ La436 X = NCH₃ La437 X = N(i-Pr) La438

X = O La439 X = S La440 X = Se La441 X = C(CH₃)₂ La442 X = NCH₃ La443 X = N(i-Pr) La444

X = O La445 X = S La446 X = Se La447 X = C(CH₃)₂ La448 X = NCH₃ La449 X = N(i-Pr) La450

X = O La451 X = S La452 X = Se La453 X = C(CH₃)₂ La454 X = NCH₃ La455 X = N(i-Pr) La456

X = O La457 X = S La458 X = Se La459 X = C(CH₃)₂ La460 X = NCH₃ La461 X = N(i-Pr) La462

X = O La463 X = S La464 X = Se La465 X = C(CH₃)₂ La466 X = NCH₃ La467 X = N(i-Pr) La468

X = O La469 X = S La470 X = Se La471 X = C(CH₃)₂ La472 X = NCH₃ La473 X = N(i-Pr) La474

X = O La475 X = S La476 X = Se La477 X = C(CH₃)₂ La478 X = NCH₃ La479 X = N(i-Pr) La480

X = O La481 X = S La482 X = Se La483 X = C(CH₃)₂ La484 X = NCH₃ La485 X = N(i-Pr) La486

X = O La487 X = S La488 X = Se La489 X = C(CH₃)₂ La490 X = NCH₃ La491 X = N(i-Pr) La492

X = O La493 X = S La494 X = Se La495 X = C(CH₃)₂ La496 X = NCH₃ La497 X = N(i-Pr) La498

X = O La499 X = S La500 X = Se La501 X = C(CH₃)₂ La502 X = NCH₃ La503 X = N(i-Pr) La504

X = O La505 X = S La506 X = Se La507 X = C(CH₃)₂ La508 X = NCH₃ La509 X = N(i-Pr) La510

X = O La511 X = S La512 X = Se La513 X = C(CH₃)₂ La514 X = NCH₃ La515 X = N(i-Pr) La516

X = O La517 X = S La518 X = Se La519 X = C(CH₃)₂ La520 X = NCH₃ La521 X = N(i-Pr) La522

X = O La523 X = S La524 X = Se La525 X = C(CH₃)₂ La526 X = NCH₃ La527 X = N(i-Pr) La528

X = O La529 X = S La530 X = Se La531 X = C(CH₃)₂ La532 X = NCH₃ La533 X = N(i-Pr) La534

X = O La535 X = S La536 X = Se La537 X = C(CH₃)₂ La538 X = NCH₃ La539 X = N(i-Pr) La540

X = O La541 X = S La542 X = Se La543 X = C(CH₃)₂ La544 X = NCH₃ La545 X = N(i-Pr) La546

X = O La547 X = S La548 X = Se La549 X = C(CH₃)₂ La550 X = NCH₃ La551 X = N(i-Pr) La552

X = O La553 X = S La554 X = Se La555 X = C(CH₃)₂ La556 X = NCH₃ La557 X = N(i-Pr) La558

X = O La559 X = S La560 X = Se La561 X = C(CH₃)₂ La562 X = NCH₃ La563 X = N(i-Pr) La564

X = O La565 X = S La566 X = Se La567 X = C(CH₃)₂ La568 X = NCH₃ La569 X = N(i-Pr) La570

X = O La571 X = S La572 X = Se La573 X = C(CH₃)₂ La574 X = NCH₃ La575 X = N(i-Pr) La576

X = O La577 X = S La578 X = Se La579 X = C(CH₃)₂ La580 X = NCH₃ La581 X = N(i-Pr) La582

X = O La583 X = S La584 X = Se La585 X = C(CH₃)₂ La586 X = NCH₃ La587 X = N(i-Pr) La588

X = O La589 X = S La590 X = Se La591 X = C(CH₃)₂ La592 X = NCH₃ La593 X = N(i-Pr) La594

X = O La595 X = S La596 X = Se La597 X = C(CH₃)₂ La598 X = NCH₃ La599 X = N(i-Pr) La600

X = O La601 X = S La602 X = Se La603 X = C(CH₃)₂ La604 X = NCH₃ La605 X = N(i-Pr) La606

X = O La607 X = S La608 X = Se La609 X = C(CH₃)₂ La610 X = NCH₃ La611 X = N(i-Pr) La612

X = O La613 X = S La614 X = Se La615 X = C(CH₃)₂ La616 X = NCH₃ La617 X = N(i-Pr) La618

X = O La619 X = S La620 X = Se La621 X = C(CH₃)₂ La622 X = NCH₃ La623 X = N(i-Pr) La624

X = O La625 X = S La626 X = Se La627 X = C(CH₃)₂ La628 X = NCH₃ La629 X = N(i-Pr) La630

X = O La631 X = S La632 X = Se La633 X = C(CH₃)₂ La634 X = NCH₃ La635 X = N(i-Pr) La636

X = O La637 X = S La638 X = Se La639 X = C(CH₃)₂ La640 X = NCH₃ La641 X = N(i-Pr) La642

X = O La643 X = S La644 X = Se La645 X = C(CH₃)₂ La646 X = NCH₃ La647 X = N(i-Pr) La648

X = O La649 X = S La650 X = Se La651 X = C(CH₃)₂ La652 X = NCH₃ La653 X = N(i-Pr) La654

X = O La655 X = S La656 X = Se La657 X = C(CH₃)₂ La658 X = NCH₃ La659 X = N(i-Pr) La660

X = O La661 X = S La662 X = Se La663 X = C(CH₃)₂ La664 X = NCH₃ La665 X = N(i-Pr) La666

X = O La667 X = S La668 X = Se La669 X = C(CH₃)₂ La670 X = NCH₃ La671 X = N(i-Pr) La672

X = O La673 X = S La674 X = Se La675 X = C(CH₃)₂ La676 X = NCH₃ La677 X = N(i-Pr) La678

X = O La679 X = S La680 X = Se La681 X = C(CH₃)₂ La682 X = NCH₃ La683 X = N(i-Pr) La684

X = O La685 X = S La686 X = Se La687 X = C(CH₃)₂ La688 X = NCH₃ La689 X = N(i-Pr) La690

X = O La691 X = S La692 X = Se La693 X = C(CH₃)₂ La694 X = NCH₃ La695 X = N(i-Pr) La696

X = O La697 X = S La698 X = Se La699 X = C(CH₃)₂ La700 X = NCH₃ La701 X = N(i-Pr) La702

X = O La703 X = S La704 X = Se La705 X = C(CH₃)₂ La706 X = NCH₃ La707 X = N(i-Pr) La708

X = O La709 X = S La710 X = Se La711 X = C(CH₃)₂ La712 X = NCH₃ La713 X = N(i-Pr) La714

X = O La715 X = S La716 X = Se La717 X = C(CH₃)₂ La718 X = NCH₃ La719 X = N(i-Pr) La720

X = O La721 X = S La722 X = Se La723 X = C(CH₃)₂ La724 X = NCH₃ La725 X = N(i-Pr) La726

X = O La727 X = S La728 X = Se La729 X = C(CH₃)₂ La730 X = NCH₃ La731 X = N(i-Pr) La732

X = O La733 X = S La734 X = Se La735 X = C(CH₃)₂ La736 X = NCH₃ La737 X = N(i-Pr) La738

X = O La739 X = S La740 X = Se La741 X = C(CH₃)₂ La742 X = NCH₃ La743 X = N(i-Pr) La744

X = O La745 X = S La746 X = Se La747 X = C(CH₃)₂ La748 X = NCH₃ La749 X = N(i-Pr) La750

X = O La751 X = S La752 X = Se La753 X = C(CH₃)₂ La754 X = NCH₃ La755 X = N(i-Pr) La756

X = O La757 X = S La758 X = Se La759 X = C(CH₃)₂ La760 X = NCH₃ La761 X = N(i-Pr) La762

X = O La763 X = S La764 X = Se La765 X = C(CH₃)₂ La766 X = NCH₃ La767 X = N(i-Pr) La768

X = O La769 X = S La770 X = Se La771 X = C(CH₃)₂ La772 X = NCH₃ La773 X = N(i-Pr) La774

X = O La775 X = S La776 X = Se La777 X = C(CH₃)₂ La778 X = NCH₃ La779 X = N(i-Pr) La780

X = O La781 X = S La782 X = Se La783 X = C(CH₃)₂ La784 X = NCH₃ La785 X = N(i-Pr) La786

X = O La787 X = S La788 X = Se La789 X = C(CH₃)₂ La790 X = NCH₃ La791 X = N(i-Pr) La792

X = O La793 X = S La794 X = Se La795 X = C(CH₃)₂ La796 X = NCH₃ La797 X = N(i-Pr) La798

X = O La799 X = S La800 X = Se La801 X = C(CH₃)₂ La802 X = NCH₃ La803 X = N(i-Pr) La804

X = O La805 X = S La806 X = Se La807 X = C(CH₃)₂ La808 X = NCH₃ La809 X = N(i-Pr) La810

X = O La811 X = S La812 X = Se La813 X = C(CH₃)₂ La814 X = NCH₃ La815 X = N(i-Pr) La816

X = O La817 X = S La818 X = Se La819 X = C(CH₃)₂ La820 X = NCH₃ La821 X = N(i-Pr) La822

X = O La823 X = S La824 X = Se La825 X = C(CH₃)₂ La826 X = NCH₃ La827 X = N(i-Pr) La828

X = O La829 X = S La830 X = Se La831 X = C(CH₃)₂ La832 X = NCH₃ La833 X = N(i-Pr) La834

X = O La835 X = S La836 X = Se La837 X = C(CH₃)₂ La838 X = NCH₃ La839 X = N(i-Pr) La840

X = O La841 X = S La842 X = Se La843 X = C(CH₃)₂ La844 X = NCH₃ La845 X = N(i-Pr) La846

X = O La847 X = S La848 X = Se La849 X = C(CH₃)₂ La850 X = NCH₃ La851 X = N(i-Pr) La852

X = O La853 X = S La854 X = Se La855 X = C(CH₃)₂ La856 X = NCH₃ La857 X = N(i-Pr) La858

X = O La859 X = S La860 X = Se La861 X = C(CH₃)₂ La862 X = NCH₃ La863 X = N(i-Pr) La864

X = O La865 X = S La866 X = Se La867 X = C(CH₃)₂ La868 X = NCH₃ La869 X = N(i-Pr) La870

X = O La871 X = S La872 X = Se La873 X = C(CH₃)₂ La874 X = NCH₃ La875 X = N(i-Pr) La876

X = O La877 X = S La878 X = Se La879 X = C(CH₃)₂ La880 X = NCH₃ La881 X = N(i-Pr) La882

X = O La883 X = S La884 X = Se La885 X = C(CH₃)₂ La886 X = NCH₃ La887 X = N(i-Pr) La888

X = O La889 X = S La890 X = Se La891 X = C(CH₃)₂ La892 X = NCH₃ La893 X = N(i-Pr) La894

X = O La895 X = S La896 X = Se La897 X = C(CH₃)₂ La898 X = NCH₃ La899 X = N(i-Pr) La900

X = O La901 X = S La902 X = Se La903 X = C(CH₃)₂ La904 X = NCH₃ La905 X = N(i-Pr) La906

X = O La907 X = S La908 X = Se La909 X = C(CH₃)₂ La910 X = NCH₃ La911 X = N(i-Pr) La912

X = O La913 X = S La914 X = Se La915 X = C(CH₃)₂ La916 X = NCH₃ La917 X = N(i-Pr) La918

X = O La919 X = S La920 X = Se La921 X = C(CH₃)₂ La922 X = NCH₃ La923 X = N(i-Pr) La924

X = O La925 X = S La926 X = Se La927 X = C(CH₃)₂ La928 X = NCH₃ La929 X = N(i-Pr) La930

X = O La931 X = S La932 X = Se La933 X = C(CH₃)₂ La934 X = NCH₃ La935 X = N(i-Pr) La936

X = O La937 X = S La938 X = Se La939 X = C(CH₃)₂ La940 X = NCH₃ La941 X = N(i-Pr) La942

X = O La943 X = S La944 X = Se La945 X = C(CH₃)₂ La946 X = NCH₃ La947 X = N(i-Pr) La948

X = O La949 X = S La950 X = Se La951 X = C(CH₃)₂ La952 X = NCH₃ La953 X = N(i-Pr) La954

X = O La955 X = S La956 X = Se La957 X = C(CH₃)₂ La958 X = NCH₃ La959 X = N(i-Pr) La960

X = O La961 X = S La962 X = Se La963 X = C(CH₃)₂ La964 X = NCH₃ La965 X = N(i-Pr) La966

X = O La967 X = S La968 X = Se La969 X = C(CH₃)₂ La970 X = NCH₃ La971 X = N(i-Pr) La972

X = O La973 X = S La974 X = Se La975 X = C(CH₃)₂ La976 X = NCH₃ La977 X = N(i-Pr) La978

X = O La979 X = S La980 X = Se La981 X = C(CH₃)₂ La982 X = NCH₃ La983 X = N(i-Pr) La984

X = O La985 X = S La986 X = Se La987 X = C(CH₃)₂ La988 X = NCH₃ La989 X = N(i-Pr) La990

X = O La991 X = S La992 X = Se La993 X = C(CH₃)₂ La994 X = NCH₃ La995 X = N(i-Pr) La996

X = O La997 X = S La998 X = Se La999 X = C(CH₃)₂ La1000 X = NCH₃ La1001 X = N(i-Pr) La1002

X = O La1003 X = S La1004 X = Se La1005 X = C(CH₃)₂ La1006 X = NCH₃ La1007 X = N(i-Pr) La1008

X = O La1009 X = S La10010 X = Se La1011 X = C(CH₃)₂ La1012 X = NCH₃ La1013 X = N(i-Pr) La1014

X = O La1015 X = S La1016 X = Se La1017 X = C(CH₃)₂ La1018 X = NCH₃ La1019 X = N(i-Pr) La1020

X = O La1021 X = S La1022 X = Se La1023 X = C(CH₃)₂ La1024 X = NCH₃ La1025 X = N(i-Pr) La1026

X = O La1027 X = S La1028 X = Se La1029 X = C(CH₃)₂ La1030 X = NCH₃ La1031 X = N(i-Pr) La1032

X = O La1033 X = S La1034 X = Se La1035 X = C(CH₃)₂ La1038 X = NCH₃ La1037 X = N(i-Pr) La1038

X = O La1039 X = S La1040 X = Se La1041 X = C(CH₃)₂ La1042 X = NCH₃ La1043 X = N(i-Pr) La1044

X = O La1045 X = S La1046 X = Se La1047 X = C(CH₃)₂ La1048 X = NCH₃ La1049 X = N(i-Pr) La1050

X = O La1051 X = S La1052 X = Se La1053 X = C(CH₃)₂ La1054 X = NCH₃ La1055 X = N(i-Pr) La1056

X = O La1057 X = S La1058 X = Se La1059 X = C(CH₃)₂ La1060 X = NCH₃ La1061 X = N(i-Pr) La1062

X = O La1063 X = S La1064 X = Se La1065 X = C(CH₃)₂ La1066 X = NCH₃ La1067 X = N(i-Pr) La1068

X = O La1069 X = S La1070 X = Se La1071 X = C(CH₃)₂ La1072 X = NCH₃ La1073 X = N(i-Pr) La1074

X = O La1075 X = S La1076 X = Se La1077 X = C(CH₃)₂ La1078 X = NCH₃ La1079 X = N(i-Pr) La1080

X = O La1081 X = S La1082 X = Se La1083 X = C(CH₃)₂ La1084 X = NCH₃ La1085 X = N(i-Pr) La1086

X = O La1087 X = S La1088 X = Se La1089 X = C(CH₃)₂ La1090 X = NCH₃ La1091 X = N(i-Pr) La1092

X = O La1093 X = S La1094 X = Se La1095 X = C(CH₃)₂ La1096 X = NCH₃ La1097 X = N(i-Pr) La1098

X = O La1099 X = S La1100 X = Se La1101 X = C(CH₃)₂ La1102 X = NCH₃ La1103 X = N(i-Pr) La1104

X = O La1105 X = S La1106 X = Se La1107 X = C(CH₃)₂ La1108 X = NCH₃ La1109 X = N(i-Pr) La1110

X = O La1111 X = S La1112 X = Se La1113 X = C(CH₃)₂ La1114 X = NCH₃ La1115 X = N(i-Pr) La1116

X = O La1117 X = S La1118 X = Se La1119 X = C(CH₃)₂ La1120 X = NCH₃ La1121 X = N(i-Pr) La1122

X = O La1123 X = S La1124 X = Se La1125 X = C(CH₃)₂ La1126 X = NCH₃ La1127 X = N(i-Pr) La1128

X = O La1129 X = S La1130 X = Se La1131 X = C(CH₃)₂ La1132 X = NCH₃ La1133 X = N(i-Pr) La1134

X = O La1135 X = S La1136 X = Se La1137 X = C(CH₃)₂ La1138 X = NCH₃ La1139 X = N(i-Pr) La1140

X = O La1141 X = S La1142 X = Se La1143 X = C(CH₃)₂ La1144 X = NCH₃ La1145 X = N(i-Pr) La1146

X = O La1147 X = S La1148 X = Se La1149 X = C(CH₃)₂ La1150 X = NCH₃ La1151 X = N(i-Pr) La1152

X = O La1153 X = S La1154 X = Se La1155 X = C(CH₃)₂ La1156 X = NCH₃ La1157 X = N(i-Pr) La1158

X = O La1159 X = S La1160 X = Se La1161 X = C(CH₃)₂ La1162 X = NCH₃ La1163 X = N(i-Pr) La1164

X = O La1165 X = S La1166 X = Se La1167 X = C(CH₃)₂ La1168 X = NCH₃ La1169 X = N(i-Pr) La1170

X = O La1171 X = S La1172 X = Se La1173 X = C(CH₃)₂ La1174 X = NCH₃ La1175 X = N(i-Pr) La1176

X = O La1177 X = S La1178 X = Se La1179 X = C(CH₃)₂ La1180 X = NCH₃ La1181 X = N(i-Pr) La1182

X = O La1183 X = S La1184 X = Se La1185 X = C(CH₃)₂ La1186 X = NCH₃ La1187 X = N(i-Pr) La1188

X = O La1189 X = S La1190 X = Se La1191 X = C(CH₃)₂ La1192 X = NCH₃ La1193 X = N(i-Pr) La1194

X = O La1195 X = S La1196 X = Se La1197 X = C(CH₃)₂ La1198 X = NCH₃ La1199 X = N(i-Pr) La1200


11. The metal complex according to claim 1, wherein the Lb and the Lc are independently selected from any one of La1 to La1307 according to claim 10, corresponding parts or complete deuterides thereof, or corresponding parts or complete fluorides thereof; and the La, the Lb, and the Lc do not have a structure of the same number.
 12. The metal complex according to any one of claims 1 to 10, wherein the Lb and the Lc are independently selected from one of the following structural formulas (a) to (k):

a dotted line refers to a bond connected to metal iridium; the number of Ra, Rb, and Rc is a maximum substitution number; the Ra, the Rb, and the Rc are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C₁-C₂₀ alkyl, substituted or unsubstituted C₃-C₃₀ cycloalkyl, substituted or unsubstituted C₁-C₃₀ heteroalkyl, substituted or unsubstituted C₇-C₃₀ aralkyl, substituted or unsubstituted C₁-C₂₀ alkoxy, substituted or unsubstituted C₆-C₃₀ aryloxy, substituted or unsubstituted C₂-C₂₀ alkenyl, substituted or unsubstituted C₃-C₃₀ silyl, substituted or unsubstituted C₆-C₃₀ aryl, substituted or unsubstituted C₃-C₃₀ heteroaryl, substituted or unsubstituted C₃-C₃₀ arylsilyl, substituted or unsubstituted C₀-C₂₀ amino, cyano, nitrile, isonitrile, and phosphino; or two adjacent substituents are optionally connected into a ring or fused structure; the “substituted” refers to substitution with deuterium, F, Cl, Br, C₁-C₁₀ alkyl, C₁-C₁₀ alkoxy, C₃-C₁₀ cycloalkyl, amino substituted with C₁-C₁₀ alkyl, C₆-C₃₀ aryl, C₇-C₃₀ aralkyl, cyano, nitrile, isonitrile, and phosphino; and a heteroatom in the heteroalkyl or heteroaryl is at least one of S, O, and N.
 13. The metal complex according to claim 12, wherein the Lb and the Lc are independently selected from the following structural formulas, corresponding parts or complete deuterides thereof, or corresponding parts or complete fluorides thereof; and the Lb and the Lc are not a ligand of the same number.


14. An electroluminescent device, comprising a cathode, an anode, and organic layers arranged between the cathode and the anode, wherein at least one of the organic layers comprises the metal complex according to any one of claims 1 to
 13. 15. The electroluminescent device according to claim 14, wherein the organic layers comprise a light-emitting layer, and the metal complex according to any one of claims 1 to 13 is used a red light-emitting doping material for the light-emitting layer; or the organic layers comprise a hole injection layer, and the metal complex according to any one of claims 1 to 13 is used as a hole injection material for the hole injection layer. 